Herbicides for citrus oil palm rubber and other plantation crops

ABSTRACT

This invention provides herbicides for use in plantation and specialty crops; and further provides novel substituted heterocyclic compounds, their agriculturally suitable compositions, and methods of using these compounds as preemergent or postemergent herbicides.

CROSS-REFERENCE TO RELATED APPLICATION

This is a division of application Ser. No. 08/256,339, filed Jul. 13, 1994, which is a 371 of PCT/US92/11330, filed Dec. 30, 1992 and a continuation-in-part of application Ser. No. 07/821,118, filed Jan. 15, 1992, now abandoned.

FIELD OF THE INVENTION

This invention relates to novel substituted heterocyclic compounds and a method for controlling undesired vegetation in crops including plantation and specialty crops. Some of the compounds of the instant invention have been disclosed previously for use generally as herbicides, but these disclosures provide no teachings for use of these compounds as herbicides in plantation crops.

BACKGROUND OF THE INVENTION

U.S. Pat. No. 4,859,229 discloses herbicidal utility in "cotton and soya" cultivations for compounds of the formula ##STR1## wherein, inter alia R¹ is H, C₁ -C₄ alkyl, C₁ -C₄ haloalkyl, formyl or C₂ -C₆ alkanoyl;

R² is (in part) an ether group;

R³ is H or CN;

R⁴ is H or halogen;

R⁵ is H, halogen or C₁ -C₄ alkyl;

R⁶ is C₁ -C₄ alkyl or C₁ -C₄ haloalkyl; and

R⁵ and R⁶ together are tri- or tetramethylene.

The instant invention provides a method for controlling undesired vegetation in plantation and specialty crops. Many of the compounds of the instant invention have been previously disclosed for use generally as herbicides, and such disclosures are found in U.S. Pat. No. 4,859,229, EP-A-438,209, JP 3-77,874 and EP-A-408,382. There are, however, no teachings for the use of these compounds as herbicides in plantation and specialty crops such as citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, plantain, pineapple, fruit trees such as apples, and nut trees. These crops are important markets and are cultivated particularly in regions of the Pacific rim and South America. Citrus, sugarcane and loblolly pine also are grown elsewhere.

The yields of selected crops such as citrus, sugarcane, coffee, banana, oil palm, loblolly pine, rubber, cocoa, grapes, fruit trees and Bermudagrass tend to be lessened by undesired plantings such as crabgrass, johnson grass, guineagrass and the like. In addition, the yields of these crops tend to be reduced by crop plants such as corn, cotton, wheat, rice, and the like. A need therefore exists for controlling these types of plantings to improve the yields of selected crops such as those mentioned above.

This invention also provides novel substituted heterocyclic compounds and their agriculturally suitable compositions which are generally useful as herbicides, as well as methods of their use as general or selective preemergent or postemergent herbicides, or as plant growth regulants.

New compounds effective for controlling the growth of undesired vegetation are in constant demand. In the most common situation, such compounds are sought to selectively control the growth of weeds in useful crops such as sugarcane, citrus, oil palm, cotton, rice, corn, wheat and soybeans, to name a few. Unchecked weed growth in such crops can cause significant losses, reducing profit to the farmer and increasing costs to the consumer. In other situations, herbicides are desired which will control all plant growth. Examples of areas in which complete control of all vegetation is desired are areas around railroad tracks, storage tanks and industrial storage areas. There are many products commercially available for these purposes, but the search continues for products which are more effective, less costly and environmentally safe.

SUMMARY OF THE INVENTION

This invention comprises a method for controlling the growth of undesired vegetation in a plantation crop by applying to the locus of the crop an effective amount of a compound of Formula I ##STR2## wherein ##STR3## A is O or S; R¹ is C₁ -C₄ alkyl optionally substituted with one or more halogen, OR⁵ SR⁶ or CN; C₃ -C₆ alkenyl or C₃ -C₆ alkynyl, each optionally substituted with 1-3 halogen; formyl; Or C₂ -C₆ alkanoyl;

R² is H, isopropyl, allyl, propargyl, CH(CH₃)C.tbd.CH, benzyl, CHR⁷ CO₂ R⁸ or may be taken together with Z;

R³ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or N(CH₃)₂ ;

R⁴ is H or halogen;

R³ and R⁴ may be taken together as --(CH₂)₃ -- or --(CH₂)₄ --;

R⁵ and R⁶ are independently H or C₁ -C₃ alkyl;

R⁷ and R⁸ are independently C₁ -C₂ alkyl;

X is Cl or Br;

Y is F or Cl;

Z is H or may be taken together with R² as ##STR4## such that the linking A atom is attached to the methine carbon; R⁹ is C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, cyclopropyl, vinyl C₂ alkynyl, CN, C(O)R¹⁰, CO₂ R¹⁰, CONR¹⁰ R¹¹, CR¹² R¹³ C(O)R¹⁰, CR¹² R¹³ CO₂ R¹⁰, CR¹² R¹³ CONR¹⁰ R¹¹, CHR¹² OH, CHR¹² OC(O)R¹⁰ or CHR¹² OC(O)NR¹⁰ R¹¹ ; and

R¹⁰, R¹¹, R¹² and R¹³ are independently H or C₁ -C₃ alkyl.

Preferred for reasons including greater herbicidal efficacy are:

1) The method wherein for Compounds of Formula I

R¹ is C₁ -C₃ alkyl optionally substituted with 1 to 3 F atoms or Cl atoms, O(C₁ -C₂ alkyl), S(C₁ -C₂ alkyl) or CN; C₃ -C₄ alkenyl optionally substituted with 1 to 3 F atoms or Cl atoms; C₃ -C₄ alkynyl; or C₂ -C₃ alkanoyl;

R² is H, isopropyl, allyl, propargyl, CH(CH₃)C.tbd.CH, CHR⁷ CO₂ R⁸ or may be taken together with Z;

R³ is C₁ -C₂ alkyl, C₁ -C₂ haloalkyl or N(CH₃)₂ ;

R⁴ is H, F, Cl or Br;

R³ and R⁴ may be taken together as --(CH₂)₃ -- or --(CH₂)₄ --; and

X is Cl.

2) The method of Preferred 1 wherein

R¹ is CH₃ optionally substituted with 1 to 3 F atoms or Cl atoms; CH₂ CN; allyl; or propargyl;

R³ is CF₃ ; and

R⁴ is H.

3) The method of Preferred 2 wherein

R⁹ is CH₃ ;

A is O; and

Q is Q-1.

Specifically Preferred for reasons of greatest herbicidal efficacy are the method of Preferred 3 which are the use of the compounds:

3-[4-chloro-2-fluoro-5-[(2-propynyl) oxy]phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H, 3H)-pyrimidinedione;

3-[4-chloro-2-fluoro-5-(2-propenyloxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H, 3H)-pyrimidinedione;

3-(5,7-dichloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H, 3H)-pyrimidinedione; and

3-( 7-choro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H, 3H)-pyrimidinedione;

and the method of Preferred 2 which is the use of the compound:

3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-6-dimethylamine-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione.

This invention also comprises compounds of Formulas II and III, agriculturally suitable compositions containing them, and their use as preemergent and/or postemergent herbicides. ##STR5## wherein A is O or S;

R¹ is C₁ -C₄ alkyl optionally substituted with one or more halogen, OR⁵, SR.sup. 6 or CN; C₃ -C₆ alkenyl or C₃ -C₆ alkynyl, each optionally substituted with 1-3 halogens; formyl; or C₂ -C₆ alkanoyl;

R² is H, isopropyl, allyl, propargyl, CH(CH₃)C.tbd.CH, benzyl, CHR⁷ CO₂ ^(R) ⁸ or may be taken together with Z;

R³ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or N(CH₃)₂ ;

R⁴ is H or halogen;

R³ and R⁴ may be taken together as --(CH₂)3-- or --(CH₂)₄ --;

R⁵ and R⁶ are independently H or C₁ -C₃ alkyl;

R⁷ and R⁸ are independently C₁ -C₂ alkyl;

X is Cl or Br;

Y is F or Cl;

Z is H or may be taken together with R² as ##STR6## such that the linking A atom is attached to the methine carbon; and R⁹ is C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, cyclopropyl, vinyl, C₂ alkynyl, CN, C(O)R¹⁰, CO₂ R¹⁰, CONR¹⁰ R¹¹, CR¹² R¹³ C(O)R¹⁰, CR¹² R¹³ CO₂ R¹⁰, CR¹² R¹³ CONR¹⁰ R¹¹, CHR¹² OH, CHR¹² OC(O)R¹⁰ or CHR¹² OC(O)NR¹⁰ R¹¹ ; and

R¹⁰, R¹¹, R¹² and R¹³ are independently H or C₁ -C₃ alkyl;

provided that

1) in compounds of Formula II, when R¹ is C₁ -C₄ alkyl optionally substituted with halogen, OR⁵ or CN; C₃ -C₄ alkenyl; formyl; or C₂ -C₆ alkanoyl; R³ is C₁ -C₄ haloalkyl; and R⁵ is C₁ -C₃ alkyl; then R² is benzyl or taken together with Z;

2) in compounds of Formula II, when R¹ is CH₂ OH or C₁ -C₃ alkyl optionally substituted with halogen; R³ is C₁ -C₄ haloalkyl; and A is S; then R² is taken together with Z;

3) in compounds of Formula III, when R¹ is C₁ -C₄ alkyl and R³ is CH₃ or CF₃ then R² is benzyl or taken together with Z;

4) in compounds of Formula II, when R¹ is C₁ -C₄ alkyl optionally substituted with halogen; formyl; or C₂ -C₆ alkanoyl; then R² is taken together with Z.

Preferred for reasons including ease of synthesis and/or greater herbicidal efficacy are:

1) Compounds of Formulas II and III wherein

R¹ is C₁ -C₃ alkyl optionally substituted with 1 to 3 F atoms or Cl atoms; O(C₁ -C₂ alkyl), S(C₁ -C₂ alkyl) or CN; C₃ -C₄ alkenyl optionally substituted with 1 to 3 F atoms or Cl atoms; C₃ -C₄ alkynyl; or C₂ -C₃ alkanoyl;

R² is H, isopropyl, allyl, propargyl, CH(CH₃)C.tbd.CH, CHR⁷ CO₂ R⁸ or may be taken together with Z;

R³ is C₁ -C₂ alkyl, C₁ -C₂ haloalkyl or N(CH₃)₂ ;

R⁴ is H, F, Cl or Br;

R³ and R⁴ may be taken together as --(CH₂)₃ -- or --(CH₂)₄ --; and

X is Cl.

2) Compounds of Preferred 1 wherein

R¹ is CH₃ optionally substituted with 1 to 3 F atoms or Cl atoms; CH₂ CN; allyl; or propargyl;

R³ is CF₃ ; and

R₄ is H.

3) Compounds of Preferred 2 wherein the compound is of Formula II;

R⁹ is CH₃ ; and

A is O.

Specifically Preferred for reasons of ease of synthesis and/or greatest herbicidal efficacy are the compound of Preferred 2 which is:

3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-6-(dimethylamino-1-methyl-1,3,5-triazine-2,4(1H, 3H)-dione;

and the compounds of Preferred 3 which are

3-(5,7-dichloro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H, 3H)-pyrimidinedione; and

3-( 7-choro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)-1-methyl-6-(trifluoromethyl)-2,4(1H, 3H)-pyrimidinedione.

In the above definitions, the term "alkyl", used either alone or in compound words such as "haloalkyl", includes straight chain or branched alkyl, e.g., methyl, ethyl, n-propyl, isopropyl or the different butyl isomers. Alkenyl includes straight chain or branched alkenes, e.g., 1-propenyl, 2-propenyl, 3-propenyl and the different butenyl isomers. The term "halogen", either alone or in compound words such as "haloalkyl", means fluorine, chlorine, bromine or iodine. Further, when used in compound words such as "haloalkyl" said alkyl may be partially or fully substituted with halogen atoms, which may be the same or different. Examples of haloalkyl include CH₂ CH₂ F, CF₂ CF₃ and CH₂ CHFCl.

DETAILED DESCRIPTION OF THE INVENTION

Many of the compounds of Formula I wherein Z and R² are not taken together can be prepared according to the procedures of U.S. Pat. No. 4,859,229 and U.S. Pat. No. 3,902,887, the disclosures of which are herein incorporated by reference.

Schemes 1 to 4 illustrate the preparation of compounds of Formula II wherein Z and R² are taken together. ##STR7##

The dihydrofuran ring of compounds of Formula II can be prepared according to the procedure of U.S. Pat. No. 4,881,967 by Claisen rearrangement of allyl ether VII followed by cyclization as shown in Scheme 1, Equations (c) and (d). The rearrangement and cyclization normally require high temperatures ranging from 100° C. to 200° C. Therefore, it is preferable to perform this process at an early stage with an inert protecting group on nitrogen. For this reason, phthalimide VII is prepared via treatment of hydroxyaniline V with phthalic anhydride IV followed by allylation of the hydroxy group of VI in the presence of a weak base such as potassium carbonate (Scheme 1, Equations (a) and (b)).

Alternatively, the compound VII can be prepared by allylation of V first followed by treatment with phthalic anhydride IV.

The rearrangement of VII can be effected by heating in an inert solvent such as N,N-dimethylaniline or ο-dichlorobenzene at a temperature of about 100° C. to 200° C. This Claisen rearrangement can also proceed with titanium tetrachloride and N-trimethylsilyl-acetanilide at ambient temperature in an inert solvent such as dichloromethane (Narasaka, K., Bald E., and Mukaiyama T.; Chemistry Letters 1975, 1041). The cyclization of VIII to give IXa can be effected by refluxing a solution of phenol VIII in an inert solvent, such as xylene, containing a catalytic to stoichiometric amount of acid such as p-toluenesulfonic acid under Dean-Stark apparatus at a temperature range of from about 120° C. to 180° C. (Scheme 1, Equation (d)). ##STR8##

For the preparation of dihydrothiophene IXb, the allylphenol VIII is treated with N,N-dimethylthiocarbamoyl chloride in the presence of a weak base such as potassium carbonate in an inert solvent such as acetone or N,N-dimethylformamide at a temperature between 0° C. and refluxing temperatures of the solvents over several hours as shown in Scheme 2a, Equation (a).

Thermal rearrangement of X may be effected in a suitable inert solvent such as ο-dichlorobenzene at 150°-250° C. to produce carbamate derivative XI. Cyclization of XI with an anhydrous acid such as hydrogen bromide in acetic acid at refluxing temperatures affords IXb as shown in Scheme 2a, Equation (c).

The acetylene substituted dihydrofuran ring of compounds of Formulas II and III (i.e., R⁹ is C₂ alkynyl) can be prepared as shown in Scheme 2b. ##STR9##

The hydroxyl group of VIII of Scheme 1, Equation (c) can be protected by a silicon protecting group using reagents such as trimethylsilyl chloride or t-butyldimethylsilyl chloride to give XXXIV. Then the reductive ozonolysis of XXXIV gives aldehyde XXXV. The diol XXXVI can be prepared by the treatment of aldehyde XXXV with lithium salt of trimethylsilylacetylene. The deprotections of both silyl protecting groups of XXXVI can be accomplished using fluoride ions such as potassium fluoride. The acetylenic hydrofuran XXXVIII can be prepared from the diol XXXVII by Mitsunobu condition using diethyl azodicarboxylate (DEAD) and triphenylphosphine according to the known procedure (Macor, J., Ryan, K., and Newman, M.; Tetrahedron 1992, 48, 1039).

The vinyl group substituted dihydrofuran ring of compounds of Formula XI and III can be prepared as shown in scheme 2c. ##STR10##

The hydroxymethyl hydrofuran XXXIX can be prepared by treatment of VIII with m-chloroperbenzoic acid (MCPBA) followed by p-toluenesulfonic acid. The treatment of XXXIX with carbon tetrabromide and triphenylphosphine gives bromomethyl hydrofuran XL. The Wittig reagent XLI can be prepared by the treatment of XL with triphenylphosphine in an inert solvent such as DMF. The vinylic hydrofuran XLII can be prepared by Wittig reaction of XLI and formaldehyde.

The hydroxy group of XXXIX can be converted to ketone, carboxylic acid, ester or amide groups by methods well known to those skilled in the art. This transformation can be carried out before or after the phthalimide protecting group is removed. If the protecting group is removed first, then the unprotected aniline derivative is first converted to the uracil or triazinedione ring (as described later) before further conversion of the hydroxyl group. ##STR11##

The phthalimide protecting group of IXa or IXb can be removed by hydrazine at ambient temperature to afford aniline XII. The formation of isocyanate XIII is accomplished by treatment of the aniline XII with phosgene or triphosgene in the presence of a base such as triethylamine at ambient temperature, or without base in an inert solvent such as dioxane or toluene at a temperature range of from 60° C. to 120° C. (Scheme 3). ##STR12##

The formation of the uracil ring in compound XV is carried out by the procedure described in U.S. Pat. No. 4,943,309. A suitable salt of an enamine XIV is treated with the isocyanate XIII at low temperature over several hours, typically between -50° C. and -70° C. in an inert solvent such as toluene, and the reaction is continued at ambient temperature for several hours. The alkylation of XV can be accomplished by treatment of XV with C₁₋₄ alkyl halide, or C₁₋₄ haloalkyl halide, especially the respective chloride or bromide, or sulphate in the presence of a base such as potassium carbonate or sodium hydride in an inert solvent such as acetone or acetonitrile at a temperature range of from about 0° C. to 120° C. The acylation of XV is carried out with acetic anhydride or a C₂₋₆ alkanecarboxylic acid halide, in the presence of base such as sodium hydride.

Schemes 5 and 6 illustrate the preparation of compounds of Formula III. ##STR13##

The formation of the triazinedione ring follows the procedure described in U.S. Pat. No. 3,902,887 when R³ is a dimethylamino group as shown in Scheme 5. N-Ethoxy-carbonylguanidine XVI is mixed with an isocyanate XVII in an inert solvent, preferably toluene, while the temperature is maintained at 25° C. to 100° C., preferably 55° C. to 80° C. The mixture of slurry containing compound XVIII is cooled, if necessary, to 24° C.-45° C., while dimethylamine is added, either as a gas or a liquid. It is preferred to add the amine at 25°-35° C., and it is important to have at least 1.0 molar equivalent and preferably, 1.0 to 2.5 molar equivalents of dimethylamine. Next a ring closure catalyst is added. The catalyst is an alkali metal alkoxide (or hydroxide) and it may be added either as a dry solid or as a solution in the alkanol. Dry sodium methoxide or a solution of sodium methoxide in methanol is a preferred catalyst. The amount of catalyst needed is from 0.1 to 5.0 mole percent of compound XVIII. The ring closure reaction can proceed at a temperature between 0° C. and 120° C. The reaction is rapid and normally complete in less than several hours. ##STR14##

When R³ is C₁ -C₄ alkyl and C₁ -C₄ haloalkyl substituents, the formation of the triazinedione ring follows the procedure described by JP 03 77,874 as shown in Scheme 6. Carbamoylation of alkylamidine hydrochloride or haloalkylamidine hydrochloride XIX with isocyanate XVII under the condition described in Scheme 5 or in the presence of NaOH in aqueous acetone gives N-phenylcarbamoyl amidine XX. The cyclocondensation of the resulting compound XX with ethyl chloroformate in the presence of base such as sodium hydride or sodium methoxide in an inert solvent such as tetrahydrofuran gives triazinedione XXII via XXI. The alkylation of XXII can be accomplished by treatment of XXII with C₁₋₄ alkyl halide, or C₁ -C₄ haloalkyl halide, especially the respective chloride, bromide or sulphate in the presence of a base such as potassium carbonate or sodium hydride in an inert solvent such as acetone or acetonitrile at a temperature range of from about 0° C. to 120° C. The acylation of XXII is carried out with acetic anhydride or a C₂ -C₆ alkanecarboxylic acid halide in the presence of base such as sodium hydride. ##STR15##

Compounds of Formula II wherein Z is hydrogen and A is oxygen can be prepared according to Scheme 7. Cyclocondensation of enamine XIV can be carried out with benzyl ether protected isocyanate XXIII. The enamine XIV wherein R³ and R⁴ are taken together as --(CH₂)₃ -- or --(CH₂)₄ -- can be prepared according to the known procedure (Kloek, J., and Leschinsky, K.; J. Org Chem., 1978, 43, 1460). Other enamines of Formula XIV wherein R³ and R⁴ are not taken together can be prepared by one skilled in the art. The resultant uracil XXIV is alkylated or acylated as described previously and benzyl ether XXV can be deprotected easily with 5 to 10% palladium on charcoal under hydrogen pressure ranging from 20 to 50 psi. The resulting phenol XXVI is treated with C₁ -C₄ alkyl halide, or C₁ -C₄ haloalkyl halide, especially the respective chloride or bromide in the presence of a base such as potassium carbonate or sodium hydride in an inert solvent such as acetone or acetonitrile at a temperature range of from about 0° C. to 120° C. to give XXVII. ##STR16##

The compound XXX which has two identical R¹⁰ substituents (wherein R¹⁰ is isopropyl, allyl or C₃ -C₄ alkynyl) can be prepared by deprotection of benzyl ether XXIV with palladium on charcoal under hydrogen followed by alkylation or acylation in the presence of base as shown in Scheme 8. ##STR17##

The same procedure can be adopted for the synthesis of triazinediones of Formula III wherein Z is hydrogen and A is oxygen as shown in Scheme 9. The cyclocondensation product XXXI from N-ethoxycarbonylguanidine XVI and benzyl ether protected isocyanate XXIII is treated with palladium on charcoal under hydrogen pressure ranging from 20 to 50 psi followed by alkylation or acylation in the presence of base to give XXXIII.

EXAMPLE 1

Preparation of 3-[4-chloro-2-fluoro-5-oxy]phenyl]-1-methyl-6-{trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

To a solution of 200 mg (0.59 mmol) of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione in 3 mL of acetonitrile was added 162 mg of potassium carbonate (1.18 mmol) and 131 mL (1.18 mmol) of an 80% solution of propargyl bromide in toluene. It was warmed under reflux for 2 h. The resulting mixture was filtered and the filtrate was concentrated in vacuo to give colorless oil which was flash chromatographed over silica gel, eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 204 mg of title compound as a white foam: ¹ H-NMR (CDC₁₃, 200 MHz) ppm 7.35 (d, 1H), 7.0 (d, 1H), 6.4 (s, 1H), 4.78 (d, 2H), 3.58 (s, 3H), 2.6 (d, 1H).

EXAMPLE 2

Preparation of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-1-methyl-1,6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

A mixture of 1.12 g (2.61 mmol) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-1-methyl-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione and 220 mg of 10% palladium on charcoal in 40 mL of ethyl acetate was placed in a Paar bottle and was agitated under 45 psi hydrogen over a 20 hour period. It was filtered and washed with 100 mL of ethyl acetate. The filtrate was concentrated in vacuo and the resultant crude product flash chromatographed over silica gel eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 521 mg of the title compound as a white foam.: ¹ -NMR (CDCl₃, 200 MHz) ppm 7.15 (d, 1H), 6.9 (d, 1H), 6.4 (s, 1H), 5.8 (s, 1H), 3.6 (s, 3H).

EXAMPLE 3

Preparation of 3-[-4-chloro-2-fluoro-5-(phenylmethoxy)-phenyl]-1-methyl-6-(trifluoromethyl) -2,4(1H,3H)-pyrimidinedione

A mixture of 1.85 g (4.46 retool) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy) phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione, 492 μL (5.20 mmol) of dimethylsulfate, and 749 mg (8.92 mmol) of sodium bicarbonate in 20 mL of acetone was warmed under reflux for 3 h. Evaporation removed the solvent to give a viscous residue. It was dissolved in 50 mL of ether and washed twice with 30 mL of water, dried (MgSO₄) and concentrated in vacuo to give white solid which was flash chromatographed over silica gel, eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 1.19 g of the title compound as a white solid, m.p.: 145°-147° C.; ¹ -NMR (CDCl₃, 200 MHz) ppm 7.4 (m, 6H), 6.85 (d, 1H), 6.4 (s, 1H), 5.1 (s, 2H), 3.55 (s, 3H) .

EXAMPLE 4

Preparation of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)-phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

To a solution of 312 mg (7.82 mmol) of sodium hydride (60% oil dispersion) in 10 mL of N,N-dimethylformamide was added 1.43 g (7.82 mmol) of ethyl-3-amino-4,4,4-trifluorocrotonate in 7 mL of toluene over a period of 30 min at -5° C. The resulting mixture was stirred for an additional 30 min before it was cooled to -70° C. Then a solution of 2.17 g (7.82 mmol) of 4-chloro-2-fluoro-5-(phenylmethoxy)phenyl isocyanate in 7 mL of toluene was added dropwise at a rate that maintained the reaction temperature below -60° C. After the addition, the thick reaction mixture was maintained at -60° C. for an additional 1 h before the cooling bath was removed. The mixture was gradually warmed to room temperature and stirring was continued for 1.5 h. Then the mixture was poured into a solution of 10 mL of concentrated HCl in 200 mL of water. The toluene layer was separated and the aqueous layer was further extracted twice with 200 mL of ether, dried (MgSO₄), concentrated in vacuo to give yellow oil which was flash chromatographed over silica gel eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 1.85 g of the title compound as a pale yellow foam: ¹ -NMR (CDCl₃, 200 MHz): ppm 7.40 (m, 6H), 6.85 (d, 1H), 6.2 (s, 1H), 5.05 (s, 2H).

EXAMPLE 5

Preparation of 3-[4-chloro-2-fluoro-5-[(2-propynyl)-oxy]phenyl]-1-(2-propynyl)-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione

To a stirred solution of 500 mg (1.50 mmol) of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione in 20 mL of acetonitrile was added 425 mg (3.1 mmol) of potassium carbonate and 0.34 mL (3.10 mmol) of 80% solution of propargyl bromide in toluene. The stirred mixture was then refluxed gently under nitrogen for 2 h. The solution was filtered, washed with ethyl acetate, and concentrated in vacuo. The resulting yellow oil was flash chromatographed over silica gel, eluting with a 1:4 v:v mixture of ethyl acetate and hexane to give 90 mg of the title compound as a pale yellow oil: ¹ -NMR (CDCl₃, 200 MHz): ppm 7.35 (d, 1H), 7.0 (d, 1H), 6.4 (s, 1H), 4.75 (m, 4H), 2.6 (m, 1H), 2.4 (m, 1H). It also gives 150 mg of 3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-1-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione as a yellow oil: ¹ -NMR (DMSO-d₆): ppm 7.7 (d, 1H), 7.4 (d, 1H), 6.4 (s, 1H), 4.8 (d, 2H), 2.5 (m, 1H).

EXAMPLE 6

Preparation of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-trifluoromethyl-2,4(1H,3H)-pyrimidinedione

A mixture of 4.27 g (10.3 mmol) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-6-(trifluoromethyl)-2,4(1H,3H)-pyrimidinedione and 420 mg of 10% palladium on charcoal in 70 mL of ethyl acetate was placed in a Paar bottle and was agitated under 45 psi hydrogen over a 16 hour period. It was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo and the resultant crude product flash chromatographed over silica gel, eluting with a 95:5 v:v mixture of dichloromethane and methanol to give 2.50 g of the title compound as a pale orange solid, m.p.: 68°-72° C.; ¹ -NMR (DMSO-d₆): ppm 7.5 (d, 1H), 7.0 (d, 1H), 6.4 (s, 1H).

EXAMPLE 7

Preparation of 3-[4-chloro-2-fluoro-5-[(2-propynyl)-oxy]phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione

To a solution of 2.80 g (8.90 mmol) of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione in 50 mL of acetone was added 1.47 g (10.7 mmol) of potassium carbonate and 1.98 mL (17.8 mmol) of an 80% solution of propargyl bromide in toluene. It was then warmed to reflux for 2 h. It was cooled to room temperature and the mixture was filtered and washed with excess ethyl acetate. The crude product was flash chromatographed over silica gel, eluting with a 3:7 v:v mixture of ethyl acetate and hexane to give 3.1 g of the title compound as a pale yellow solid, m.p.: 61°-65° C.; ¹ -NMR (CDCl₃, 200 MHz) ppm 7.0 (d, 1H), 4.75 (m, 2H), 3.45 (s, 3H), 3.1 (s, 6H), 2.6 (m, 1H).

EXAMPLE 8

Preparation of 3-[4-chloro-2-fluoro-5-(hydroxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione

A mixture of 4.62 g (11.4 mmol) of 3-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione and 460 mg of 10% palladium on charcoal in 50 mL of ethyl acetate was placed in a Paar bottle and was agitated under 45 psi hydrogen over a 14 hour period. It was filtered and washed with ethyl acetate. The filtrate was concentrated in vacuo and the resultant crude product flash chromatographed over silica gel eluting with a 1:1 v:v mixture of ethyl acetate and hexane to give 3.2 g of the title compound as a pale grey solid, m.p.: 247°-249° C. (dec); ¹ -NMR (DMSO-d₆) ppm 7.45 (d, 1H), 6.95 (d, 1H), 3.3 (s, 3H), 3.0 (s, 6H).

EXAMPLE 9

Preparation of 5-[4-chloro-2-fluoro-5-(phenylmethoxy)-phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione

To a solution of 5.05 g (29.2 mmol) of N-ethoxy-carbonyl-N,N', N"-trimethylguanidine in 25 mL of toluene was added a solution of 7.72 g (27.8 mmol) of 4-chloro-2-fluoro-5-(phenylmethoxy)phenyl isocyanate in 50 mL of toluene over a period of 30 min while maintaining the temperature between 55° C. and 80° C. It was then stirred at the same temperature for an hour. To a solution of the resulting N-[N-[4-chloro-2-fluoro-5-(phenylmethoxy)phenyl]carbamoyl-N', N'-dimethylamidino]-N-methylcarbamate in toluene was added 3.21 g (71.5 mmol) of dimethylamine in 10 mL of toluene at room temperature. While the temperature was between 25° C. and 40° C., 45 mg (0.834 mmol) of sodium methoxide was added. After 30 min, it was quenched with 100 mL of water. The aqueous layer was extracted with ethyl acetate. The combined organic layers were washed with 0.1N hydrochloric acid, brine, and water, dried (MgSO₄) and Concentrated in vacuo. The crude product was flash chromatographed over silica gel eluting with a 1:1 v:v mixture of ethyl acetate and hexane to give 5.3 g of the title compound as a brown solid, m.p.: 193°-194° C.; ¹ -NMR (CDCl₃, 200 MHZ) ppm 7.4 (m, 6H), 6.95 (d, 1H), 5.05 (d, 2H), 3.45 (s, 3H), 3.1 (s, 6H).

Using the procedures outlined in Schemes 1-9, and Examples 1-9, the compounds of this invention including the compounds of Tables I-III can readily be prepared by one skilled in the art.

                  TABLE I                                                          ______________________________________                                          ##STR18##                                                                     R.sup.1    R.sup.2     R.sup.3  R.sup.4                                                                            A   X    Y                                 ______________________________________                                         CH.sub.3   H           CF.sub.3 H   O   Cl   F                                 CH.sub.3   H           CF.sub.3 H   S   Cl   F                                 CH.sub.3   H           CF.sub.3 H   O   Cl   Cl                                CH.sub.3   H           CF.sub.3 H   S   Cl   Cl                                CH.sub.3   H           CF.sub.3 Br  O   Cl   F                                 CH.sub.3   H           CF.sub.3 Br  S   Cl   F                                 CH.sub.3   H           CF.sub.3 Br  O   Cl   Cl                                CH.sub.3   H           CF.sub.3 Br  S   Cl   Cl                                CH.sub.3   CH.sub.2 Ph CF.sub.3 H   O   Cl   F                                 CH.sub.3   CH.sub.2 Ph CF.sub.3 H   S   Cl   F                                 CH.sub.3   CH.sub.2 Ph CF.sub.3 H   O   Cl   Cl                                CH.sub.3   CH.sub.2 Ph CF.sub.3 H   S   Cl   Cl                                CH.sub.3   CH.sub.2 Ph CF.sub.3 Br  O   Cl   F                                 CH.sub.3   CH.sub.2 Ph CF.sub.3 Br  S   Cl   F                                 CH.sub.3   CH.sub.2 Ph CF.sub.3 Br  O   Cl   Cl                                CH.sub.3   CH.sub.2 Ph CF.sub.3 Br  S   Cl   Cl                                CH.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   F                                 CH.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   F                                 CH.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   Cl                                CH.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   Cl                                CH.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 Br  O   Cl   F                                 CH.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 Br  S   Cl   F                                 CH.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 Br  O   Cl   Cl                                CH.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 Br  S   Cl   Cl                                CH.sub.3   iPr         CF.sub.3 H   O   Cl   F                                 CH.sub.3   iPr         CF.sub.3 H   S   Cl   F                                 CH.sub.3   iPr         CF.sub.3 H   O   Cl   Cl                                CH.sub.3   iPr         CF.sub.3 H   S   Cl   Cl                                CH.sub.3   iPr         CF.sub.3 Br  O   Cl   F                                 CH.sub.3   iPr         CF.sub.3 Br  S   Cl   F                                 CH.sub.3   iPr         CF.sub.3 Br  O   Cl   Cl                                CH.sub.3   iPr         CF.sub.3 Br  S   Cl   Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 H   O   Cl   F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 H   S   Cl   F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 H   O   Cl   Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 H   S   Cl   Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 Br  O   Cl   F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 Br  S   Cl   F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 Br  O   Cl   Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 Br  S   Cl   Cl                                CF.sub.3   H           CF.sub.3 H   O   Cl   F                                 CF.sub.3   H           CF.sub.3 H   S   Cl   F                                 CF.sub.3   H           CF.sub.3 H   O   Cl   Cl                                CF.sub.3   H           CF.sub.3 H   S   Cl   Cl                                CF.sub.3   H           CF.sub.3 Br  O   Cl   F                                 CF.sub.3   H           CF.sub.3 Br  S   Cl   F                                 CF.sub.3   H           CF.sub.3 Br  O   Cl   Cl                                CF.sub.3   H           CF.sub.3 Br  S   Cl   Cl                                CF.sub.3   CH.sub.2 Ph CF.sub.3 H   O   Cl   F                                 CF.sub.3   CH.sub.2 Ph CF.sub.3 H   S   Cl   F                                 CF.sub.3   CH.sub.2 Ph CF.sub.3 H   O   Cl   Cl                                CF.sub.3   CH.sub.2 Ph CF.sub.3 H   S   Cl   Cl                                CF.sub.3   CH.sub.2 Ph CF.sub.3 Br  O   Cl   F                                 CF.sub.3   CH.sub.2 Ph CF.sub.3 Br  S   Cl   F                                 CF.sub.3   CH.sub.2 Ph CF.sub.3 Br  O   Cl   Cl                                CF.sub.3   CH.sub.2 Ph CF.sub.3 Br  S   Cl   Cl                                CF.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   F                                 CF.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   F                                 CF.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   Cl                                CF.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   Cl                                CF.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 Br  O   Cl   F                                 CF.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 Br  S   Cl   F                                 CF.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 Br  O   Cl   Cl                                CF.sub.3   CH.sub.2 CCH                                                                               CF.sub.3 Br  S   Cl   Cl                                CF.sub.3   iPr         CF.sub.3 H   O   Cl   F                                 CF.sub.3   iPr         CF.sub.3 H   S   Cl   F                                 CF.sub.3   iPr         CF.sub.3 H   O   Cl   Cl                                CF.sub.3   iPr         CF.sub.3 H   S   Cl   Cl                                CF.sub.3   iPr         CF.sub.3 Br  O   Cl   F                                 CF.sub.3   iPr         CF.sub.3 Br  S   Cl   F                                 CF.sub.3   iPr         CF.sub.3 Br  O   Cl   Cl                                CF.sub.3   iPr         CF.sub.3 Br  S   Cl   Cl                                CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 H   O   Cl   F                                 CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 H   S   Cl   F                                 CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 H   O   Cl   Cl                                CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 H   S   Cl   Cl                                CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 Br  O   Cl   F                                 CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 Br  S   Cl   F                                 CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 Br  O   Cl   Cl                                CF.sub.3   CH.sub.2 CCH.sub.2                                                                         CF.sub.3 Br  S   Cl   Cl                                CH.sub.2 CCH                                                                              H           CF.sub.3 H   O   Cl   F                                 CH.sub.2 CCH                                                                              H           CF.sub.3 H   S   Cl   F                                 CH.sub.2 CCH                                                                              H           CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CCH                                                                              H           CF.sub.3 H   S   Cl   Cl                                CH.sub.2 CCH                                                                              H           CF.sub.3 Br  O   Cl   F                                 CH.sub.2 CCH                                                                              H           CF.sub.3 Br  S   Cl   F                                 CH.sub.2 CCH                                                                              H           CF.sub.3 Br  O   Cl   Cl                                CH.sub.2 CCH                                                                              H           CF.sub.3 Br  S   Cl   Cl                                CH.sub.2 CCH                                                                              CH.sub.2 Ph CF.sub.3 H   O   Cl   F                                 CH.sub.2 CCH                                                                              CH.sub.2 Ph CF.sub.3 H   S   Cl   F                                 CH.sub.2 CCH                                                                              CH.sub.2 Ph CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CCH                                                                              CH.sub.2 Ph CF.sub.3 H   S   Cl   Cl                                CH.sub.2 CCH                                                                              CH.sub.2 Ph CF.sub.3 Br  O   Cl   F                                 CH.sub.2 CCH                                                                              CH.sub.2 Ph CF.sub.3 Br  S   Cl   F                                 CH.sub.2 CCH                                                                              CH.sub.2 Ph CF.sub.3 Br  O   Cl   Cl                                CH.sub.2 CCH                                                                              CH.sub.2 Ph CF.sub.3 Br  S   Cl   Cl                                CH.sub.2 CCH                                                                              CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   F                                 CH.sub.2 CCH                                                                              CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   F                                 CH.sub.2 CCH                                                                              CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CCH                                                                              CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   Cl                                CH.sub.2 CCH                                                                              CH.sub.2 CCH                                                                               CF.sub.3 Br  O   Cl   F                                 CH.sub.2 CCH                                                                              CH.sub.2 CCH                                                                               CF.sub.3 Br  S   Cl   F                                 CH.sub.2 CCH                                                                              CH.sub.2 CCH                                                                               CF.sub.3 Br  O   Cl   Cl                                CH.sub.2 CCH                                                                              CH.sub.2 CCH                                                                               CF.sub.3 Br  S   Cl   Cl                                CH.sub.2 CCH                                                                              iPr         CF.sub.3 H   O   Cl   F                                 CH.sub.2 CCH                                                                              iPr         CF.sub.3 H   S   Cl   F                                 CH.sub.2 CCH                                                                              iPr         CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CCH                                                                              iPr         CF.sub.3 H   S   Cl   Cl                                CH.sub.2 CCH                                                                              iPr         CF.sub.3 Br  O   Cl   F                                 CH.sub.2 CCH                                                                              iPr         CF.sub.3 Br  S   Cl   F                                 CH.sub.2 CCH                                                                              iPr         CF.sub.3 Br  O   Cl   Cl                                CH.sub.2 CCH                                                                              iPr         CF.sub.3 Br  S   Cl   Cl                                CH.sub.2 CCH                                                                              CH.sub.2 CCH.sub.2                                                                         CF.sub.3 H   O   Cl   F                                 CH.sub.2 CCH                                                                              CH.sub.2 CCH.sub.2                                                                         CF.sub.3 H   S   Cl   F                                 CH.sub.2 CCH                                                                              CH.sub.2 CCH.sub.2                                                                         CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CCH                                                                              CH.sub.2 CCH.sub.2                                                                         CF.sub.3 H   S   Cl   Cl                                CH.sub.2 CCH                                                                              CH.sub.2 CCH.sub.2                                                                         CF.sub.3 Br  O   Cl   F                                 CH.sub.2 CCH                                                                              CH.sub.2 CCH.sub.2                                                                         CF.sub.3 Br  S   Cl   F                                 CH.sub.2 CCH                                                                              CH.sub.2 CCH.sub.2                                                                         CF.sub.3 Br  O   Cl   Cl                                CH.sub.2 CCH                                                                              CH.sub.2 CCH.sub.2                                                                         CF.sub.3 Br  S   Cl   Cl                                CH.sub.2 CCF                                                                              CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CCF                                                                              CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   F                                 CH.sub.2 CCF                                                                              CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   Cl                                CH.sub.2 CCF                                                                              CH.sub.2 Ph CF.sub.3 H   O   Cl   F                                 CH.sub.2 CCF                                                                              CH.sub.2 Ph CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CCF                                                                              CH.sub.2 Ph CF.sub.3 H   S   Cl   F                                 CH.sub.2 CCF                                                                              CH.sub.2 Ph CF.sub.3 H   S   Cl   Cl                                CH.sub.2 CCF                                                                              H           CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CCF                                                                              H           CF.sub.3 H   S   Cl   F                                 CH.sub.2 CCF                                                                              H           CF.sub.3 H   S   Cl   Cl                                CH.sub.2 CCF                                                                              H           CF.sub.3 H   O   Cl   F                                 CH.sub.2 CCF                                                                              iPr         CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CCF                                                                              iPr         CF.sub.3 H   S   Cl   F                                 CH.sub.2 CCF                                                                              iPr         CF.sub.3 H   S   Cl   Cl                                CH.sub.2 CCF                                                                              iPr         CF.sub.3 H   O   Cl   F                                 CH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   F                                 CH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CHCH.sub.2                                                                       CH.sub.2 Ph CF.sub.3 H   O   Cl   F                                 CH.sub.2 CHCH.sub.2                                                                       CH.sub.2 Ph CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CHCH.sub.2                                                                        CF.sub.3 H   O   Cl   F                                 CH.sub.2 CHCH.sub.2                                                                       CH.sub.2 CHCH.sub.2                                                                        CF.sub.3 H   O   Cl   Cl                                CHF.sub.2  H           N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CHF.sub.2  H           N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CHF.sub.2  H           N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CHF.sub.2  H           N(CH.sub.3).sub.2                                                                       H   S   Cl   Cl                                CHF.sub.2  H           N(CH.sub.3).sub.2                                                                       Br  O   Cl   F                                 CHF.sub.2  H           N(CH.sub.3).sub.2                                                                       Br  S   Cl   F                                 CHF.sub.2  H           N(CH.sub.3).sub.2                                                                       Br  O   Cl   Cl                                CHF.sub.2  H           N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       H   S   Cl   Cl                                CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       Br  O   Cl   F                                 CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       Br  S   Cl   F                                 CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       Br  O   Cl   Cl                                CHF.sub.2  CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                CHF.sub.2  CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CHF.sub.2  CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CHF.sub.2  CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CHF.sub.2  CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   S   Cl   Cl                                CHF.sub.2  CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       Br  O   Cl   F                                 CHF.sub.2  CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       Br  S   Cl   F                                 CHF.sub.2  CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       Br  O   Cl   Cl                                CHF.sub.2  CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                       E   S   Cl   F                                 CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                       H   S   Cl   Cl                                CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                       Br  O   Cl   F                                 CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                       Br  S   Cl   F                                 CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                       Br  O   Cl   Cl                                CHF.sub.2  iPr         N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       H   S   Cl   Cl                                CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       Br  O   Cl   F                                 CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       Br  S   Cl   F                                 CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       Br  O   Cl   Cl                                CHF.sub.2  CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                CH.sub.3   H           N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CH.sub.3   H           N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CH.sub.3   H           N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CH.sub.3   H           N(CH.sub.3).sub.2                                                                       H   S   Cl   Cl                                CH.sub.3   H           N(CH.sub.3).sub.2                                                                       Br  O   Cl   F                                 CH.sub.3   H           N(CH.sub.3).sub.2                                                                       Br  S   Cl   F                                 CH.sub.3   H           N(CH.sub.3).sub.2                                                                       Br  O   Cl   Cl                                CH.sub.3   H           N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       H   S   Cl   Cl                                CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       Br  O   Cl   F                                 CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       Br  S   Cl   F                                 CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       Br  O   Cl   Cl                                CH.sub.3   CH.sub.2 Ph N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                CH.sub.3   CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CH.sub.3   CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CH.sub.3   CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CH.sub.3   CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   S   Cl   Cl                                CH.sub.3   CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       Br  O   Cl   F                                 CH.sub.3   CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       Br  S   Cl   F                                 CH.sub.3   CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       Br  O   Cl   Cl                                CH.sub.3   CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                       H   S   Cl   Cl                                CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                       Br  O   Cl   F                                 CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                       Br  S   Cl   F                                 CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                       Br  O   Cl   Cl                                CH.sub.3   iPr         N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       H   S   Cl   Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       Br  O   Cl   F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       Br  S   Cl   F                                 CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       Br  O   Cl   Cl                                CH.sub.3   CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.3                                                                          O   Cl   F                                   CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.3                                                                          S   Cl   F                                   CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.3                                                                          O   Cl   Cl                                  CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.3                                                                          S   Cl   Cl                                  CH.sub.3   CH.sub.2 CCH                                                                               (CH.sub.2).sub.3                                                                          O   Cl   F                                   CH.sub.3   CH.sub.2 CCH                                                                               (CH.sub.2).sub.3                                                                          S   Cl   F                                   CH.sub.3   CH.sub.2 CCH                                                                               (CH.sub.2).sub.3                                                                          O   Cl   Cl                                  CH.sub.3   CH.sub.2 CCH                                                                               (CH.sub.2).sub.3                                                                          S   Cl   Cl                                  CH.sub.3   iPr         (CH.sub.2).sub.3                                                                          O   Cl   F                                   CH.sub.3   iPr         (CH.sub.2).sub.3                                                                          S   Cl   F                                   CH.sub.3   iPr         (CH.sub.2).sub.3                                                                          O   Cl   Cl                                  CH.sub.3   iPr         (CH.sub.2).sub.3                                                                          S   Cl   Cl                                  CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.4                                                                          O   Cl   F                                   CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.4                                                                          S   Cl   F                                   CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.4                                                                          O   Cl   Cl                                  CH.sub.3   CH.sub.2 Ph (CH.sub.2).sub.4                                                                          S   Cl   Cl                                  CH.sub.3   CH.sub.2 CCH                                                                               (CH.sub.2).sub.4                                                                          O   Cl   F                                   CH.sub.3   CH.sub.2 CCH                                                                               (CH.sub.2).sub.4                                                                          S   Cl   F                                   CH.sub.3   CH.sub.2 CCH                                                                               (CH.sub.2).sub.4                                                                          O   Cl   Cl                                  CH.sub.3   CH.sub.2 CCH                                                                               (CH.sub.2).sub.4                                                                          S   Cl   Cl                                  CH.sub.3   iPr         (CH.sub.2).sub.4                                                                          O   Cl   F                                   CH.sub.3   iPr         (CH.sub.2).sub.4                                                                          S   Cl   F                                   CH.sub.3   iPr         (CH.sub.2).sub.4                                                                          O   Cl   Cl                                  CH.sub.3   iPr         (CH.sub.2).sub.4                                                                          S   Cl   Cl                                  CN         CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   F                                 CN         CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   F                                 CN         CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CN         CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                COCH.sub.3 CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   F                                 COCH.sub.3 CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   F                                 COCH.sub.3 CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                COCH.sub.3 CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                COCH.sub.3 iPr         N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 COCH.sub.3 iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 COCH.sub.3 iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                COCH3      iPr         N(CH.sub.3).sub.2                                                                       Br  O   Cl   F                                 COCF.sub.3 CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   F                                 COCF.sub.3 CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   Cl                                COCF.sub.3 CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   F                                 COCF.sub.3 iPr         N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 COCF.sub.3 iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                COCF.sub.3 iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 OCH.sub.3  CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   F                                 OCH.sub.3  CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   F                                 OCH.sub.3  CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                OCH.sub.3  CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                CF.sub.2 H CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   F                                 CF.sub.2 H CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   F                                 CF.sub.2 H CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CF.sub.2 H CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       Br  S   Cl   Cl                                CF.sub.2 H iPr         N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CF.sub.2 H iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CF.sub.2 H iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CF.sub.2 H iPr         N(CH.sub.3).sub.2                                                                       Br  O   Cl   F                                 n-Bu       CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   F                                 n-Bu       CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   Cl                                n-Bu       CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   F                                 n-Bu       iPr         N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 n-Bu       iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                n-Bu       iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CHMeCCH    CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   F                                 CHMeCCH    CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   Cl                                CHMeCCH    CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   F                                 CHMeCCH    CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CHMeCCH    CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CHMeCCH    CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CHMeCCH    iPr         CF.sub.3 H   S   Cl   F                                 CHMeCCH    iPr         CF.sub.3 H   O   Cl   Cl                                CHMeCCH    iPr         CF.sub.3 H   O   Cl   F                                 CHMeCCH    iPr         N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CHMeCCH    iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CHMeCCH    iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   F                                 CH.sub.2 CMeCH.sub.2                                                                      CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CH.sub.2 CMeCH.sub.2                                                                      CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CH.sub.2 CMeCH.sub.2                                                                      CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CH.sub.2 CMeCH.sub.2                                                                      CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CMeCH.sub.2                                                                      CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   F                                 CH.sub.2 CMeCH.sub.2                                                                      CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CMeCH.sub.2                                                                      iPr         N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CH.sub.2 CMeCH.sub.2                                                                      iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CH.sub.2 CMeCH.sub.2                                                                      iPr         N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CH.sub.2 CMeCH.sub.2                                                                      iPr         CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CMeCH.sub.2                                                                      iPr         CF.sub.3 H   S   Cl   F                                 CH.sub.2 CMeCH.sub.2                                                                      iPr         CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CMeCH.sub.2                                                                      CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CH.sub.2 CMeCH.sub.2                                                                      CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                CH.sub.2 CMeCH.sub.2                                                                      CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 CH.sub.2 CMeCH.sub.2                                                                      CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   Cl                                CH.sub.2 CMeCH.sub.2                                                                      CH.sub.2 CCH                                                                               CF.sub.3 H   S   Cl   F                                 CH.sub.2 CMeCH.sub.2                                                                      CH.sub.2 CCH                                                                               CF.sub.3 H   O   Cl   Cl                                iPr        iPr         N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 iPr        iPr         N(CH.sub.3).sub.2                                                                       H   O   Cl   Cl                                iPr        iPr         N(CH.sub.3).sub.2                                                                       H   S   Cl   F                                 iPr        iPr         CF.sub.3 H   O   Cl   Cl                                iPr        iPr         CF.sub.3 H   S   Cl   F                                 iPr        iPr         CF.sub.3 H   O   Cl   Cl                                ______________________________________                                    

                  TABLE II                                                         ______________________________________                                          ##STR19##                                                                     R.sup.9 = CH.sub.3 unless otherwise noted                                      ______________________________________                                         R.sup.1     R.sup.3   R.sup.4 A     X    Y                                     ______________________________________                                         CH.sub.3    CF.sub.3  H       O     Cl   F                                     CH.sub.3    CF.sub.3  H       S     Cl   F                                     CH.sub.3    CF.sub.3  H       O     Cl   Cl                                    CH.sub.3    CF.sub.3  H       S     Cl   Cl                                    CH.sub.3    N(CH.sub.3).sub.2                                                                        H       O     Cl   F                                     CH.sub.3    N(CH.sub.3).sub.2                                                                        H       S     Cl   F                                     CH.sub.3    N(CH.sub.3).sub.2                                                                        H       O     Cl   Cl                                    CH.sub.3    N(CH.sub.3).sub.2                                                                        H       S     Cl   Cl                                    CH.sub.3    CF.sub.3  Br      O     Cl   F                                     CH.sub.3    CF.sub.3  Br      S     Cl   F                                     CH.sub.3    CF.sub.3  Br      O     Cl   Cl                                    CH.sub.3    CF.sub.3  Br      S     Cl   Cl                                    CH.sub.3    N(CH.sub.3).sub.2                                                                        Br      O     Cl   F                                     CH.sub.3    N(CH.sub.3).sub.2                                                                        Br      S     Cl   F                                     CH.sub.3    N(CH.sub.3).sub.2                                                                        Br      O     Cl   Cl                                    CH.sub.3    N(CH.sub.3).sub.2                                                                        Br      S     Cl   Cl                                    CH.sub.3    (CH.sub.2).sub.3                                                                             O       Cl   F                                       CH.sub.3    (CH.sub.2).sub.3                                                                             O       Cl   Cl                                      CH.sub.3    (CH.sub.2).sub.3                                                                             S       Cl   F                                       CH.sub.3    (CH.sub.2).sub.3                                                                             S       Cl   Cl                                      CH.sub.3    (CH.sub.2).sub.4                                                                             O       Cl   F                                       CH.sub.3    (CH.sub.2).sub.4                                                                             O       Cl   F                                       CH.sub.3    (CH.sub.2).sub.4                                                                             S       Cl   F                                       CH.sub.3    (CH.sub.2).sub.4                                                                             S       Cl   F                                       CF.sub.3    CF.sub.3  H       O     Cl   F                                     CF.sub.3    CF.sub.3  H       S     Cl   F                                     CF.sub.3    CF.sub.3  H       O     Cl   Cl                                    CF.sub.3    CF.sub.3  H       S     Cl   Cl                                    CF.sub.3    N(CH.sub.3).sub.2                                                                        H       O     Cl   F                                     CF.sub.3    N(CH.sub.3).sub.2                                                                        H       S     Cl   F                                     CT3         N(CH.sub.3).sub.2                                                                        H       O     Cl   Cl                                    CF.sub.3    N(CH.sub.3).sub.2                                                                        H       S     Cl   Cl                                    CF.sub.3    CF.sub.3  Br      O     Cl   F                                     CF.sub.3    CF.sub.3  Br      S     Cl   F                                     CF.sub.3    CF.sub.3  Br      O     Cl   Cl                                    CF.sub.3    CF.sub.3  Br      S     Cl   Cl                                    CF.sub.3    N(CH.sub.3).sub.2                                                                        Br      O     Cl   F                                     CF.sub.3    N(CH.sub.3).sub.2                                                                        Br      S     Cl   F                                     CF.sub.3    N(CH.sub.3).sub.2                                                                        Br      O     Cl   Cl                                    CF.sub.3    N(CH.sub.3).sub.2                                                                        Br      S     Cl   Cl                                    CF.sub.3    (CH.sub.2).sub.3                                                                             O       Cl   F                                       CF.sub.3    (CH.sub.2).sub.3                                                                             O       Cl   Cl                                      CF.sub.3    (CH.sub.2).sub.3                                                                             S       Cl   F                                       CF.sub.3    (CH.sub.2).sub.3                                                                             S       Cl   Cl                                      CF.sub.3    (CH.sub.2).sub.4                                                                             O       Cl   F                                       CF.sub.3    (CH.sub.2).sub.4                                                                             O       Cl   F                                       CF.sub.3    (CH.sub.2).sub.4                                                                             S       Cl   F                                       CF.sub.3    (CH.sub.2).sub.4                                                                             S       Cl   F                                       CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H       O     Cl   F                                     CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H       S     Cl   F                                     CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H       O     Cl   Cl                                    CH.sub.2 CCH.sub.2                                                                         CF.sub.3  H       O     Cl   F                                     CH.sub.2 CCH.sub.2                                                                         CHF.sub.2 H       0     Cl   F                                     CH.sub.2 CCH.sub.2                                                                         CHF.sub.2 H       O     Cl   Cl                                    CH.sub.2 CCH.sub.2                                                                         CHF.sub.2 H       S     Cl   F                                     CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        H       O     Cl   F                                     CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        H       S     Cl   F                                     CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        H       O     Cl   Cl                                    CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        H       S     Cl   Cl                                    CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br      O     Cl   F                                     CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br      S     Cl   F                                     CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br      O     Cl   Cl                                    CH.sub.2 CCH.sub.2                                                                         CF.sub.3  Br      S     Cl   Cl                                    CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        Br      O     Cl   F                                     CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        Br      S     Cl   F                                     CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        Br      O     Cl   Cl                                    CH.sub.2 CCH.sub.2                                                                         N(CH.sub.3).sub.2                                                                        Br      S     Cl   Cl                                    CH.sub.2 CCH.sub.2                                                                         (CH.sub.2).sub.3                                                                             O       Cl   F                                       CH.sub.2 CCH.sub.2                                                                         (CH.sub.2).sub.3                                                                             O       Cl   Cl                                      CH.sub.2 CCH.sub.2                                                                         (CH.sub.2).sub.3                                                                             S       Cl   F                                       CH.sub.2 CCH.sub.2                                                                         (CH.sub.2).sub.3                                                                             S       Cl   Cl                                      CH.sub.2 CCH.sub.2                                                                         (CH.sub.2).sub.4                                                                             O       Cl   F                                       CH.sub.2 CCH.sub.2                                                                         (CH.sub.2).sub.4                                                                             O       Cl   F                                       CH.sub.2 CCH.sub.2                                                                         (CH.sub.2).sub.4                                                                             S       Cl   F                                       CH.sub.2 CCH.sub.2                                                                         (CH.sub.2).sub.4                                                                             S       Cl   F                                       CH.sub.2 CCH                                                                               CF.sub.3  H       O     Cl   F                                     CH.sub.2 CCH                                                                               CF.sub.3  H       S     Cl   F                                     CH.sub.2 CCH                                                                               CF.sub.3  H       O     Cl   Cl                                    CH.sub.2 CCH                                                                               CF.sub.3  H       O     Cl   F                                     CH.sub.2 CCH                                                                               CHF.sub.2 H       O     Cl   F                                     CH.sub.2 CCH                                                                               CHF.sub.2 H       O     Cl   Cl                                    CH.sub.2 CCH                                                                               CHF.sub.2 H       S     Cl   F                                     CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                        H       O     Cl   F                                     CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                        H       S     Cl   F                                     CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                        H       O     Cl   Cl                                    CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                        H       S     Cl   Cl                                    CH.sub.2 CCH                                                                               CF.sub.3  Br      O     Cl   F                                     CH.sub.2 CCH                                                                               CF.sub.3  Br      S     Cl   F                                     CH.sub.2 CCH                                                                               CF.sub.3  Br      O     Cl   Cl                                    CH.sub.2 CCH                                                                               CF.sub.3  Br      S     Cl   Cl                                    CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                        Br      O     Cl   F                                     CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                        Br      S     Cl   F                                     CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                        Br      O     Cl   Cl                                    CH.sub.2 CCH                                                                               N(CH.sub.3).sub.2                                                                        Br      S     Cl   Cl                                    CH.sub.2 CCH                                                                               (CH.sub.2).sub.3                                                                             O       Cl   F                                       CH.sub.2 CCH                                                                               (CH.sub.2).sub.3                                                                             O       Cl   Cl                                      CH.sub.2 CCH                                                                               (CH.sub.2).sub.3                                                                             S       Cl   F                                       CH.sub.2 CCH                                                                               (CH.sub.2).sub.3                                                                             S       Cl   Cl                                      CH.sub.2 CCH                                                                               (CH.sub.2).sub.4                                                                             O       Cl   F                                       CH.sub.2 CCH                                                                               (CH.sub.2).sub.4                                                                             O       Cl   F                                       CH.sub.2 CCH                                                                               (CH.sub.2).sub.4                                                                             S       Cl   F                                       CH.sub.2 CCH                                                                               (CH.sub.2).sub.4                                                                             S       Cl   F                                       CH.sub.2 CCH                                                                               CF.sub.3  F       O     Cl   F                                     CH.sub.2 CCH                                                                               CF.sub.3  F       O     Cl   Cl                                    n-Bu        CF.sub.3  H       O     Cl   F                                     n-Bu        CF.sub.3  H       S     Cl   F                                     COCH.sub.3  CF.sub.3  H       O     Cl   F                                     COCH.sub.3  CF.sub.3  H       O     Cl   Cl                                    CN          CF.sub.3  H       O     Cl   F                                     CN          CF.sub.3  H       O     Cl   Cl                                    CHF.sub.2   CF.sub.3  H       O     Cl   F                                     CHF.sub.2   CF.sub.3  H       O     Cl   Cl                                    CH.sub.3    CHF.sub.2 Br      O     Cl   F                                     CH.sub.3    CHF.sub.2 Br      S     Cl   F                                     CH.sub.3    CF.sub.3  F       O     Cl   F                                     CH.sub.3    CF.sub.3  F       S     Cl   F                                     CH.sub.3    CHF.sub.2 F       O     Cl   F                                     CH.sub.3    CHF.sub.2 F       S     Cl   F                                     CH.sub.3    CH.sub.2 F                                                                               F       O     Cl   F                                     CH.sub.3    CH.sub.2 F                                                                               F       S     Cl   F                                     CH.sub.3    CF.sub.3  Cl      O     Cl   F                                     CH.sub.3    CF.sub.3  Cl      S     Cl   F                                     CH.sub.3    CF.sub.3  Cl      O     Cl   F                                     CH.sub.3    CF.sub.3  Cl      S     Cl   F                                     ______________________________________                                         R.sup.1                                                                              R.sup.3   R.sup.4                                                                               A    X    Y    R.sup.9                                  ______________________________________                                         CH.sub.3                                                                             CF.sub.3  H      O    Cl   F    CH.sub.2 CH.sub.3                        CH.sub.3                                                                             CF.sub.3  H      S    Cl   F    CH.sub.2 CH.sub.3                        CH.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CH.sub.2 CH.sub.3                        CH.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CH.sub.2 CH.sub.3                        CH.sub.3                                                                             CF.sub.3  H      O    Cl   F    CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3                                                                             CF.sub.3  H      S    Cl   F    CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3                                                                             CF.sub.3  H      O    Cl   F    CF.sub.3                                 CH.sub.3                                                                             CF.sub.3  H      S    Cl   F    CF.sub.3                                 CH.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CF.sub.3                                 CH.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CF.sub.3                                 CH.sub.3                                                                             CF.sub.3  H      O    Cl   F    CF.sub.2 H                               CH.sub.3                                                                             CF.sub.3  H      S    Cl   F    CF.sub.2 H                               CH.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CF.sub.2 H                               CH.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CF.sub.2 H                               CH.sub.3                                                                             CF.sub.3  H      O    Cl   F    CFH.sub.2                                CH.sub.3                                                                             CF.sub.3  H      S    Cl   F    CFH.sub.2                                CH.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CFH.sub.2                                CH.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CFH.sub.2                                CH.sub.3                                                                             CF.sub.3  H      O    Cl   F    CHCH.sub.2                               CH.sub.3                                                                             CF.sub.3  H      S    Cl   F    CHCH.sub.2                               CH.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CHCH.sub.2                               CH.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CHCH.sub.2                               CH.sub.3                                                                             CF.sub.3  H      O    Cl   F    CCH                                      CH.sub.3                                                                             CF.sub.3  H      S    Cl   F    CCH                                      CH.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CCH                                      CH.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CCH                                      CH.sub.3                                                                             CF.sub.3  H      O    Cl   F    CN                                       CH.sub.3                                                                             CF.sub.3  H      S    Cl   F    CN                                       CH.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CN                                       CH.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CN                                       CF.sub.3                                                                             CF.sub.3  H      O    Cl   F    CH.sub.2 CH.sub.3                        CF.sub.3                                                                             CF.sub.3  H      S    Cl   F    CH.sub.2 CH.sub.3                        CF.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CH.sub.2 CH.sub.3                        CF.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CH.sub.2 CH.sub.3                        CF.sub.3                                                                             CF.sub.3  H      O    Cl   F    CH.sub.2 CH.sub.2 CH.sub.3               CF.sub.3                                                                             CF.sub.3  H      S    Cl   F    CH.sub.2 CH.sub.2 CH.sub.3               CF.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CH.sub.2 CH.sub.2 CH.sub.3               CF.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CH.sub.2 CH.sub.2 CH.sub.3               CF.sub.3                                                                             CF.sub.3  H      O    Cl   F    CF.sub.3                                 CF.sub.3                                                                             CF.sub.3  H      S    Cl   F    CF.sub.3                                 CF.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CF.sub.3                                 CF.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CF.sub.3                                 CF.sub.3                                                                             CF.sub.3  H      O    Cl   F    CF.sub.2 H                               CF.sub.3                                                                             CF.sub.3  H      S    Cl   F    CF.sub.2 H                               CF.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CF.sub.2 H                               CF.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CF.sub.2 H                               CF.sub.3                                                                             CF.sub.3  H      O    Cl   F    CFH.sub.2                                CF.sub.3                                                                             CF.sub.3  H      S    Cl   F    CFH.sub.2                                CF.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CFH.sub.2                                CF.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CFH.sub.2                                CF.sub.3                                                                             CF.sub.3  H      O    Cl   F    CHCH.sub.2                               CF.sub.3                                                                             CF.sub.3  H      S    Cl   F    CHCH.sub.2                               CF.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CHCH.sub.2                               CF.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CHCH.sub.2                               CF.sub.3                                                                             CF.sub.3  H      O    Cl   F    CCH                                      CF.sub.3                                                                             CF.sub.3  H      S    Cl   F    CCH                                      CF.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CCH                                      CF.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CCH                                      CF.sub.3                                                                             CF.sub.3  H      O    Cl   F    CN                                       CF.sub.3                                                                             CF.sub.3  H      S    Cl   F    CN                                       CF.sub.3                                                                             CF.sub.3  H      O    Cl   Cl   CN                                       CF.sub.3                                                                             CF.sub.3  H      S    Cl   Cl   CN                                       CH.sub.3                                                                             CF.sub.3  Br     O    Cl   F    CH.sub.2 CH.sub.3                        CH.sub.3                                                                             CF.sub.3  Br     S    Cl   F    CH.sub.2 CH.sub.3                        CH.sub.3                                                                             CF.sub.3  Br     O    Cl   Cl   CH.sub.2 CH.sub.3                        CH.sub.3                                                                             CF.sub.3  Br     S    Cl   Cl   CH.sub.2 CH.sub.3                        CH.sub.3                                                                             CF.sub.3  Br     O    Cl   F    CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3                                                                             CF.sub.3  Br     S    Cl   F    CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3                                                                             CF.sub.3  Br     O    Cl   Cl   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3                                                                             CF.sub.3  Br     S    Cl   Cl   CH.sub.2 CH.sub.2 CH.sub.3               CH.sub.3                                                                             CF.sub.3  Br     O    Cl   F    CF.sub.3                                 CH.sub.3                                                                             CF.sub.3  Br     S    Cl   F    CF.sub.3                                 CH.sub.3                                                                             CF.sub.3  Br     O    Cl   Cl   CF.sub.3                                 CH.sub.3                                                                             CF.sub.3  Br     S    Cl   Cl   CF.sub.3                                 CH.sub.3                                                                             CF.sub.3  Br     O    Cl   F    CF.sub.2 H                               CH.sub.3                                                                             CF.sub.3  Br     S    Cl   F    CF.sub.2 H                               CH.sub.3                                                                             CF.sub.3  Br     O    Cl   Cl   CF.sub.2 H                               CH.sub.3                                                                             CF.sub.3  Br     S    Cl   Cl   CF.sub.2 H                               CH.sub.3                                                                             CF.sub.3  Br     O    Cl   F    CFH.sub.2                                CH.sub.3                                                                             CF.sub.3  Br     S    Cl   F    CFH.sub.2                                CH.sub.3                                                                             CF.sub.3  Br     O    Cl   Cl   CFH.sub.2                                CH.sub.3                                                                             CF.sub.3  Br     S    Cl   Cl   CFH.sub.2                                CH.sub.3                                                                             CF.sub.3  Br     O    Cl   F    CHCH.sub.2                               CH.sub.3                                                                             CF.sub.3  Br     S    Cl   F    CHCH.sub.2                               CH.sub.3                                                                             CF.sub.3  Br     O    Cl   Cl   CHCH.sub.2                               CH.sub.3                                                                             CF.sub.3  Br     S    Cl   Cl   CHCH.sub.2                               CH.sub.3                                                                             CF.sub.3  Br     O    Cl   F    CCH                                      CH.sub.3                                                                             CF.sub.3  Br     S    Cl   F    CCH                                      CH.sub.3                                                                             CF.sub.3  Br     O    Cl   Cl   CCH                                      CH.sub.3                                                                             CF.sub.3  Br     S    Cl   Cl   CCH                                      CH.sub.3                                                                             CF.sub.3  Cl     O    Cl   F    CHCH.sub.2                               CH.sub.3                                                                             CF.sub.3  Cl     S    Cl   F    CHCH.sub.2                               CH.sub.3                                                                             CF.sub.3  Cl     O    Cl   Cl   CHCH.sub.2                               CH.sub.3                                                                             CF.sub.3  Cl     S    Cl   Cl   CHCH.sub.2                               CH.sub.3                                                                             CF.sub.3  Cl     O    Cl   F    CCH                                      CH.sub.3                                                                             CF.sub.3  Cl     S    Cl   F    CCH                                      CH.sub.3                                                                             CF.sub.3  Cl     O    Cl   Cl   CCH                                      CH.sub.3                                                                             CF.sub.3  Cl     S    Cl   Cl   CCH                                      CH.sub.3                                                                             CF.sub.3  Br     O    Cl   F    CN                                       CH.sub.3                                                                             CF.sub.3  Br     S    Cl   F    CN                                       CH.sub.3                                                                             CF.sub.3  Br     O    Cl   Cl   CN                                       CH.sub.3                                                                             CF.sub.3  Br     S    Cl   Cl   CN                                       CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   F    CH.sub.2 CH.sub.3                          CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   F    CH.sub.2 CH.sub.3                          CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   Cl   CH.sub.2 CH.sub.3                          CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   F    CH.sub.2 CH.sub.3                          CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   F    CH.sub.2 CH.sub.3                          CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   F    CH.sub.2 CH.sub.3                          CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   Cl   CH.sub.2 CH.sub.3                          CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   Cl   CH.sub.2 CH.sub.3                          CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   F    CF.sub.3                                   CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   F    CF.sub.3                                   CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   Cl   CF.sub.3                                   CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   Cl   CF.sub.3                                   CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   F    CF.sub.3                                   CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   F    CF.sub.3                                   CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   Cl   CF.sub.3                                   CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   Cl   CF.sub.3                                   CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   F    CF.sub.2 H                                 CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   F    CF.sub.2 H                                 CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   Cl   CF.sub.2 H                                 CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   Cl   CF.sub.2 H                                 CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   F    CF.sub.2 H                                 CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   F    CF.sub.2 H                                 CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   Cl   CF.sub.2 H                                 CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   Cl   CF.sub.2 H                                 CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   F    CFH.sub.2                                  CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   F    CFH.sub.2                                  CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   Cl   CFH.sub.2                                  CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   Cl   CFH.sub.2                                  CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   F    CFH.sub.2                                  CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   F    CFH.sub.2                                  CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   Cl   CFH.sub.2                                  CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   Cl   CFH.sub.2                                  CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   F    CHCH.sub.2                                 CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   F    CHCH.sub.2                                 CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   Cl   CHCH.sub.2                                 CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   Cl   CHCH.sub.2                                 CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   F    CHCH.sub.2                                 CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   F    CHCH.sub.2                                 CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   Cl   CHCH.sub.2                                 CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   Cl   CHCH.sub.2                                 CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   F    CCH                                        CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   F    CCH                                        CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   Cl   CCH                                        CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   Cl   CCH                                        CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   F    CCH                                        CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   F    CCH                                        CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   Cl   CCH                                        CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   Cl   CCH                                        CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   F    CN                                         CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   F    CN                                         CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            O      Cl   Cl   CN                                         CH.sub.3                                                                             (CH.sub.2).sub.3                                                                            S      Cl   Cl   CN                                         CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   F    CN                                         CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   F    CN                                         CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            O      Cl   Cl   CN                                         CH.sub.3                                                                             (CH.sub.2).sub.4                                                                            S      Cl   Cl   CN                                         CH.sub.3                                                                             CF.sub.3  H      O    Cl   F    CH.sub.2 OH                              CH.sub.3                                                                             CF.sub.3  H      O    Cl   F    CH.sub.2 OC(O)CH.sub.3                   CH.sub.3                                                                             CF.sub.3  H      O    Cl   F    CO.sub.2 CH.sub.3                        CH.sub.3                                                                             CF.sub.3  H      O    Cl   F    CON(CH.sub.3).sub.2                      CH.sub.3                                                                             N(CH.sub.3).sub.2                                                                        H      O    Cl   F    CH.sub.2 OH                              CH.sub.3                                                                             N(CH.sub.3).sub.2                                                                        H      O    Cl   F    CH.sub.2 OC(O)CH.sub.3                   CH.sub.3                                                                             N(CH.sub.3).sub.2                                                                        H      O    Cl   F    CO.sub.2 CH.sub.3                        CH.sub.3                                                                             CF.sub.3  Br     O    Cl   F    CH.sub.2 OH                              CH.sub.3                                                                             CF.sub.3  Br     O    Cl   F    CH.sub.2 OC(O)CH.sub.3                   CH.sub.3                                                                             CF.sub.3  Br     O    Cl   F    CO.sub.2 CH.sub.3                        CH.sub.3                                                                             CF.sub.3  Br     S    Cl   F    CH.sub.2 OH                              ______________________________________                                    

                                      TABLE III                                    __________________________________________________________________________      ##STR20##                                                                     R.sup.1  R.sup.3                                                                              A  X   Y  R.sup.2  Z                                            __________________________________________________________________________     CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  H        H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl H        H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  H        H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl H        H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH.sub.2 CCH                                                                            H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH.sub.2 CCH                                                                            H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH.sub.2 CCH                                                                            H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH.sub.2 CCH                                                                            H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH.sub.2 Ph                                                                             H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH.sub.2 Ph                                                                             H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH.sub.2 Ph                                                                             H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH.sub.2 Ph                                                                             H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  iPr      H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl iPr      H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  iPr      H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl iPr      H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CHMeCH   H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CHMeCCH  H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CHMeCCH  H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CHMeCCH  H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CHMeCO.sub.2 Me                                                                         H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CHMeCO.sub.2 Me                                                                         H                                            CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CH.sub.3)CH.sub.2                                  CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CH.sub.3)CH.sub.2                                  CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CH.sub.3 CF.sub.3                                                                             O  Cl  F  H        H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  Cl H        H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  F  H        H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  Cl H        H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  F  CH.sub.2 CCH                                                                            H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  Cl CH.sub.2 CCH                                                                            H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  F  CH.sub.2 CCH                                                                            H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  Cl CH.sub.2 CCH                                                                            H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  F  CH.sub.2 Ph                                                                             H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  Cl CH.sub.2 Ph                                                                             H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  F  CH.sub.2 Ph                                                                             H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  Cl CH.sub.2 Ph                                                                             H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  F  iPr      H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  Cl iPr      H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  F  iPr      H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  Cl iPr      H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  F  CHMeCCH  H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  Cl CHMeCCH  H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  F  CHMeCCH  H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  Cl CHMeCCH  H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  Cl CHMeCO.sub.2 Me                                                                         H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            CH.sub.3 CF.sub.3                                                                             S  Cl  Cl CHMeCO.sub.2 Me                                                                         H                                            CH.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CH.sub.3)CH.sub.2                                  CH.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CH.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CH.sub.3)CH.sub.2                                  CH.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  H        H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl H                                                     CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  H        H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl H        H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH.sub.2 CCH                                                                            H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH.sub.2 CCH                                                                            H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH.sub.2 CCH                                                                            H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH.sub.2 CCH                                                                            H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH.sub.2 Ph                                                                             H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH.sub.2 Ph                                                                             H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH.sub.2 Ph                                                                             H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH.sub.2 Ph                                                                             H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  iPr      H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl iPr      H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  iPr      H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl iPr      H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CHMeCCH  H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CHMeCCH  H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CHMeCCH  H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CHMeCCH  H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CHMeCO.sub.2 Me                                                                         H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CHMeCo.sub.2 Me                                                                         H                                            CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CH.sub.3)CH.sub.2                                  CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CH.sub.3)CH.sub.2                                  CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CF.sub.3 CF.sub.3                                                                             O  Cl  F  H        H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  Cl H        H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  F  H        H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  Cl H        H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  F  CH.sub.2 CCH                                                                            H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  Cl CH.sub.2 CCH                                                                            H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  F  CH.sub.2 CCH                                                                            H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  Cl CH.sub.2 CCH                                                                            H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  F  CH.sub.2 Ph                                                                             H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  Cl CH.sub.2 Ph                                                                             H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  F  CH.sub.2 Ph                                                                             H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  Cl CH.sub.2 Ph                                                                             H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  F  Pr       H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  Cl Pr       H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  F  Pr       H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  Cl Pr       H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  F  CHMeCCH  H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  Cl CHMeCCH  H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  F  CHMeCCH  H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  Cl CHMeCCH  H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  F  CHMeCo.sub.2 Me                                                                         H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  Cl CHMeCo.sub.2 Me                                                                         H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  F  CHMeCo.sub.2 Me                                                                         H                                            CF.sub.3 CF.sub.3                                                                             S  Cl  Cl CHMeCo.sub.2 Me                                                                         H                                            CF.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CH.sub.3)CH.sub.2                                  CF.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CF.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CH.sub.3)CH.sub.2                                  CF.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CH.sub.3)CH.sub.2                                  i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  F  H        H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  Cl H        H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  F  H        H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  Cl H        H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  F  CH.sub.2 CCH                                                                            H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH.sub.2 CCH                                                                            H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  F  CH.sub.2 CCH                                                                            H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH.sub.2 CCH                                                                            H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  F  CH.sub.2 Ph                                                                             H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH.sub.2 Ph                                                                             H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  F  CH.sub.2 Ph                                                                             H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH.sub.2 Ph                                                                             H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  F  iPr      H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  Cl iPr      H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  F  iPr      H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  Cl iPr      H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  F  CHMeCCH  H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  Cl CHMeCCH  H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  F  CHMeCCH  H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  Cl CHMeCCH  H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  Cl CHMeCO.sub.2 Me                                                                         H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  Cl CHMeCO.sub.2 Me                                                                         H                                            i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CH.sub.3)CH.sub.2                                  i-Pr     N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CH.sub.3)CH.sub.2                                  i-Pr     N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CH.sub.3)CH.sub.2                                  i-Pr     CF.sub.3                                                                             O  Cl  F  H        H                                            i-Pr     CF.sub.3                                                                             O  Cl  Cl H        H                                            i-Pr     CF.sub.3                                                                             S  Cl  F  H        H                                            i-Pr     CF.sub.3                                                                             S  Cl  Cl H        H                                            i-Pr     CF.sub.3                                                                             O  Cl  F  CH.sub.2 CCH                                                                            H                                            i-Pr     CF.sub.3                                                                             O  Cl  Cl CH.sub.2 CCH                                                                            H                                            i-Pr     CF.sub.3                                                                             S  Cl  F  CH.sub.2 CCH                                                                            H                                            i-Pr     CF.sub.3                                                                             S  Cl  Cl CH.sub.2 CCH                                                                            H                                            i-Pr     CF.sub.3                                                                             O  Cl  F  CH.sub.2 Ph                                                                             H                                            i-Pr     CF.sub.3                                                                             O  Cl  Cl CH.sub.2 Ph                                                                             H                                            i-Pr     CF.sub.3                                                                             S  Cl  F  CH.sub.2 Ph                                                                             H                                            i-Pr     CF.sub.3                                                                             S  Cl  Cl CH.sub.2 Ph                                                                             H                                            i-Pr     CF.sub.3                                                                             O  Cl  F  iPr      H                                            i-Pr     CF.sub.3                                                                             O  Cl  Cl iPr      H                                            i-Pr     CF.sub.3                                                                             S  Cl  F  iPr      H                                            i-Pr     CF.sub.3                                                                             S  Cl  Cl iPr      H                                            i-Pr     CF.sub.3                                                                             O  Cl  F  CHMeCCH  H                                            i-Pr     CF.sub.3                                                                             O  Cl  Cl CHMeCCH  H                                            i-Pr     CF.sub.3                                                                             S  Cl  F  CHMeCCH  H                                            i-Pr     CF.sub.3                                                                             S  Cl  Cl CHMeCCH  H                                            i-Pr     CF.sub.3                                                                             O  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            i-Pr     CF.sub.3                                                                             O  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            i-Pr     CF.sub.3                                                                             S  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            i-Pr     CF.sub.3                                                                             S  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            i-Pr     CF.sub.3                                                                             O  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            i-Pr     CF.sub.3                                                                             O  Cl  Cl CHMeCO.sub.2 Me                                                                         H                                            i-Pr     CF.sub.3                                                                             S  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            i-Pr     CF.sub.3                                                                             S  Cl  Cl CHMeCO.sub.2 Me                                                                         H                                            i-Pr     CF.sub.3                                                                             O  Cl  F  CH(CH.sub.3)CH.sub.2                                  i-Pr     CF.sub.3                                                                             O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  i-Pr     CF.sub.3                                                                             S  Cl  F  CH(CH.sub.3)CH.sub.2                                  i-Pr     CF.sub.3                                                                             S  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  F  H        H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  Cl H        H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  F  H        H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  Cl H        H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  F  CH.sub.2 CCH                                                                            H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH.sub.2 CCH                                                                            H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  F  CH.sub.2 CCH                                                                            H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH.sub.2 CCH                                                                            H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  F  CH.sub.2 Ph                                                                             H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH.sub.2 Ph                                                                             H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  F  CH.sub.2 Ph                                                                             H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH.sub.2 Ph                                                                             H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  F  iPr      H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  Cl iPr      H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  F  iPr      H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  Cl iPr      H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  F  CHMeCCH  H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  Cl CHMeCCH  H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  F  CHMeCCH  H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  Cl CHMeCCH  H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  Cl CHMeCO.sub.2 Me                                                                         H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  Cl CHMeCO.sub.2 Me                                                                         H                                            CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CH.sub.3)CH.sub.2                                  CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CH.sub.3)CH.sub.2                                  CH.sub.2 CCH                                                                            N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  F  H        H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  Cl H        H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  F  H        H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  Cl H        H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  F  CH.sub.2 CCH                                                                            H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  Cl CH.sub.2 CCH                                                                            H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  F  CH.sub.2 CCH                                                                            H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  Cl CH.sub.2 CCH                                                                            H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  F  CH.sub.2 Ph                                                                             H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  Cl CH.sub.2 Ph                                                                             H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  F  CH.sub.2 Ph                                                                             H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  Cl CH.sub.2 Ph                                                                             H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  F  iPr      H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  Cl iPr      H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  F  iPr      H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  Cl iPr      H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  F  CHMeCCH  H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  Cl CHMeCCH  H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  F  CHMeCCH  H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  Cl CHMeCCH  H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  F  CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  Cl CH.sub.2 CHCH.sub.2                                                                     H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  Cl CHMeCO.sub.2 Me                                                                         H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  F  CHMeCO.sub.2 Me                                                                         H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  Cl CHMeCO.sub.2 Me                                                                         H                                            CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  F  CH(CH.sub.3)CH.sub.2                                  CH.sub.2 CCH                                                                            CF.sub.3                                                                             O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  F  CH(CH.sub.3)CH.sub.2                                  CH.sub.2 CCH                                                                            CF.sub.3                                                                             S  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CHO      CF.sub.3                                                                             O  Cl  F  CHMeCCH  H                                            CHO      CF.sub.3                                                                             O  Cl  Cl CHMeCCH  H                                            CHO      CF.sub.3                                                                             O  Cl  F  CH(CH.sub.3)CH.sub.2                                  CHO      CF.sub.3                                                                             O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  COCH.sub.3                                                                              CF.sub.3                                                                             O  ClF    CHMeCCH  H                                            COCH.sub.3                                                                              CF.sub.3                                                                             O  ClCl   CHMeCCH  H                                            COCH.sub.3                                                                              CF.sub.3                                                                             O  ClF    CH(CH.sub.3)CH.sub.2                                  COCH.sub.3                                                                              CF.sub.3                                                                             O  ClCl   CH(CH.sub.3)CH.sub.2                                  COCH.sub.3                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  F  CHMeCCH  H                                            COCH.sub.3                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  Cl CHMeCCH  H                                            COCH.sub.3                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CH.sub.3)CH.sub.2                                  COCH.sub.3                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CHF.sub.2                                                                               CF.sub.3                                                                             O  Cl  F  CHMeCCH  H                                            CHF.sub.2                                                                               CF.sub.3                                                                             O  Cl  Cl CHMeCCH  H                                            CHF.sub.2                                                                               CF.sub.3                                                                             O  Cl  F  CH(CH.sub.3)CH.sub.2                                  CHF.sub.2                                                                               CF.sub.3                                                                             O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CHF.sub.2                                                                               N(CH.sub.3).sub.2                                                                    O  ClF    CHMeCCH  H                                            CHF.sub.2                                                                               N(CH.sub.3).sub.2                                                                    O  ClCl   CHMeCCH  H                                            CHF.sub.2                                                                               N(CH.sub.3).sub.2                                                                    O  ClF    CH(CH.sub.3)CH.sub.2                                  CHF.sub.2                                                                               N(CH.sub.3).sub.2                                                                    O  ClCl   CH(CH.sub.3)CH.sub.2                                  CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  F  CHMeCCH  H                                            CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  Cl CHMeCCH  H                                            CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  F  CH(CH.sub.3)CH.sub.2                                  CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  F  CHMeCCH  H                                            CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  CHMeCCH                                                                           H                                                     CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CH.sub.3)CH.sub.2                                  CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CHMeCCH  N(CH.sub.3).sub.2                                                                    O  Cl  F  CHMeCCH  H                                            CHMeCCH  N(CH.sub.3).sub.2                                                                    O  Cl  Cl CHMeCCH  H                                            CHMeCCH  N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CH.sub.3)CH.sub.2                                  CHMeCCH  N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CH.sub.3)CH.sub.2                                  CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CF.sub.3)CH.sub.2                                  CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CF.sub.3)CH.sub.2                                  CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CF.sub.3)CH.sub.2                                  CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CF.sub.3)CH.sub.2                                  CH.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CF.sub.3)CH.sub.2                                  CH.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CF.sub.3)CH.sub.2                                  CH.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CF.sub.3)CH.sub.2                                  CH.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CF.sub.3)CH.sub.2                                  CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CF.sub.3)CH.sub.2                                  CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CF.sub.3)CH.sub.2                                  CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CF.sub.3)CH.sub.2                                  CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CF.sub.3)CH.sub.2                                  CF.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CF.sub.3)CH.sub.2                                  CF.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CF.sub.3)CH.sub.2                                  CF.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CF.sub.3)CH.sub.2                                  CF.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CF.sub.3)CH.sub.2                                  CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CF.sub.3)CH.sub.2                                  CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CF.sub.3)CH.sub.2                                  CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CF.sub.3)CH.sub.2                                  CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CF.sub.3)CH.sub.2                                  CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  F  CH(CF.sub.3)CH.sub.2                                  CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  Cl CH(CF.sub.3)CH.sub.2                                  CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  F  CH(CF.sub.3)CH.sub.2                                  CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  Cl CH(CF.sub.3)CH.sub.2                                  CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CHCH.sub.2)CH.sub.2                                CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CHCH.sub.2)CH.sub.2                                CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CHCH.sub.2)CH.sub.2                                CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CHCH.sub.2)CH.sub.2                                CH.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CHCH.sub.2)CH.sub.2                                CH.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CHCH.sub.2)CH.sub.2                                CH.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CHCH.sub.2)CH.sub.2                                CH.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CHCH.sub.2)CH.sub.2                                CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CHCH.sub.2)CH.sub.2                                CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CHCH.sub.2)CH.sub.2                                CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CHCH.sub.2)CH.sub.2                                CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CHCH.sub.2)CH.sub.2                                CF.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CHCH.sub.2)CH.sub.2                                CF.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CHCH.sub.2)CH.sub.2                                CF.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CHCH.sub.2)CH.sub.2                                CF.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CHCH.sub.2)CH.sub.2                                CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CHCH.sub.2)CH.sub.2                                CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CHCH.sub.2)CH.sub.2                                CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CHCH.sub.2)CH.sub.2                                CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CHCH.sub.2)CH.sub.2                                CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  F  CH(CHCH.sub.2)CH.sub.2                                CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  Cl CH(CHCH.sub.2)CH.sub.2                                CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  F  CH(CHCH.sub.2)CH.sub.2                                CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  Cl CH(CHCH.sub.2)CH.sub.2                                CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CCH)CH.sub.2                                       CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CCH)CH.sub.2                                       CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CCH)CH.sub.2                                       CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CCH)CH.sub.2                                       CH.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CCH)CH.sub.2                                       CH.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CCH)CH.sub.2                                       CH.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CCH)CH.sub.2                                       CH.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CCH)CH.sub.2                                       CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CCH)CH.sub.2                                       CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CCH)CH.sub.2                                       CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CCH)CH.sub.2                                       CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CCH)CH.sub.2                                       CF.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CCH)CH.sub.2                                       CF.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CCH)CH.sub.2                                       CF.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CCH)CH.sub.2                                       CF.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CCH)CH.sub.2                                       CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CCH)CH.sub.2                                       CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CCH)CH.sub.2                                       CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CCH)CH.sub.2                                       CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CCH)CH.sub.2                                       CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  F  CH(CCH)CH.sub.2                                       CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  Cl CH(CCH)CH.sub.2                                       CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  F  CH(CCH)CH.sub.2                                       CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  Cl CH(CCH)CH.sub.2                                       CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CH.sub.2 CH.sub.3)CH.sub.2                         CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CH.sub.2 CH.sub.3)CH.sub.2                         CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CH.sub.2 CH.sub.3)CH.sub.2                         CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CH.sub.2 CH.sub.3)CH.sub.2                         CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CH.sub.2 CH.sub.3)CH.sub.2                         CF.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CH.sub.2 CH.sub.3)CH.sub.2                         CF.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CH.sub.2 CH.sub.3)CH.sub.2                         CF.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CH.sub.2 CH.sub.3)CH.sub.2                         CF.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  F  CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  Cl CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  F  CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  Cl CH(CH.sub.2 CH.sub.3)CH.sub.2                         CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CH.sub.2 F)CH.sub.2                                CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CH.sub.2 F)CH.sub.2                                CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CH.sub.2 F)CH.sub.2                                CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CH.sub.2 F)CH.sub.2                                CH.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CH.sub.2 F)CH.sub.2                                CH.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CH.sub.2 F)CH.sub.2                                CH.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CH.sub.2 F)CH.sub.2                                CH.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CH.sub.2 F)CH.sub.2                                CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CH.sub.2 F)CH.sub.2                                CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CH.sub.2 F)CH.sub.2                                CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CH.sub.2 F)CH.sub.2                                CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CH.sub.2 F)CH.sub.2                                CF.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CH.sub.2 F)CH.sub.2                                CF.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CH.sub.2 F)CH.sub.2                                CF.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CH.sub.2 F)CH.sub.2                                CF.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CH.sub.2 F)CH.sub.2                                CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CH.sub.2 F)CH.sub.2                                CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CH.sub.2 F)CH.sub.2                                CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CH.sub.2 F)CH.sub.2                                CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CH.sub.2 F)CH.sub.2                                CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  F  CH(CH.sub.2 F)CH.sub.2                                CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  Cl CH(CH.sub.2 F)CH.sub.2                                CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  F  CH(CH.sub.2 F)CH.sub.2                                CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  Cl CH(CH.sub.2 F)CH.sub.2                                CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CN)CH.sub.2                                        CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CN)CH.sub.2                                        CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CN)CH.sub.2                                        CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CN)CH.sub.2                                        CH.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CN)CH.sub.2                                        CH.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CN)CH.sub.2                                        CH.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CN)CH.sub.2                                        CH.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CN)CH.sub.2                                        CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CN)CH.sub.2                                        CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CN)CH.sub.2                                        CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CN)CH.sub.2                                        CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CN)CH.sub.2                                        CF.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CN)CH.sub.2                                        CF.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CH)CH.sub.2                                        CF.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CN)CH.sub.2                                        CF.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CN)CH.sub.2                                        CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CN)CH.sub.2                                        CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CN)CH.sub.2                                        CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CN)CH.sub.2                                        CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CN)CH.sub.2                                        CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  F  CH(CN)CH.sub.2                                        CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  Cl CH(CN)CH.sub.2                                        CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  F  CH(CN)CH.sub.2                                        CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  Cl CH(CN)CH.sub.2                                        CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CF.sub.2 H)CH.sub.2                                CH.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CF.sub.2 H)CH.sub.2                                CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CF.sub.2 H)CH.sub.2                                CH.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CF.sub.2 H)CH.sub.2                                CH.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CF.sub.2 H)CH.sub.2                                CH.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CF.sub.2 H)CH.sub.2                                CH.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CF.sub.2 H)CH.sub.2                                CH.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CF.sub.2 H)CH.sub.2                                CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CF.sub.2 H)CH.sub.2                                CF.sub.3 N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CF.sub.2 H)CH.sub.2                                CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CF.sub.2 H)CH.sub.2                                CF.sub.3 N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CF.sub.2 H)CH.sub.2                                CF.sub.3 CF.sub.3                                                                             O  Cl  F  CH(CF.sub.2 H)CH.sub.2                                CF.sub.3 CF.sub.3                                                                             O  Cl  Cl CH(CF.sub.2 H)CH.sub.2                                CF.sub.3 CF.sub.3                                                                             S  Cl  F  CH(CF.sub.2 H)CH.sub.2                                CF.sub.3 CF.sub.3                                                                             S  Cl  Cl CH(CF.sub.2 H)CH.sub.2                                CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  F  CH(CF.sub.2 H)CH.sub.2                                CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    O  Cl  Cl CH(CF.sub.2 H)CH.sub.2                                CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  F  CH(CF.sub.2 H)CH.sub.2                                CH.sub.2 F                                                                              N(CH.sub.3).sub.2                                                                    S  Cl  Cl CH(CF.sub.2 H)CH.sub.2                                CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  F  CH(CF.sub.2 H)CH.sub.2                                CH.sub.2 F                                                                              CF.sub.3                                                                             O  Cl  Cl CH(CF.sub.2 H)CH.sub.2                                CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  F  CH(CF.sub.2 H)CH.sub.2                                CH.sub.2 F                                                                              CF.sub.3                                                                             S  Cl  Cl CH(CF.sub.2 H)CH.sub.2                                __________________________________________________________________________

Formulation

Compounds of this invention will generally be used in formulation with an agriculturally suitable carrier comprising a liquid or solid diluent or an organic solvent. Use formulations include dusts, granules, pellets, solutions, suspensions, emulsions, wettable powders, emulsifiable concentrates, dry flowables and the like, consistent with the physical properties of the active ingredient, mode of application and environmental factors such as soil type, moisture and temperature. Sprayable formulations can be extended in suitable media and used at spray volumes from about one to several hundred liters per hectare. High strength compositions are primarily used as intermediates for further formulation. The formulations will typically contain effective amounts of active ingredient, diluent and surfactant within the following approximate ranges which add up 100 weight percent.

    ______________________________________                                                     Weight Percent                                                                 Active                                                                         Ingredient                                                                             Diluent   Surfactant                                       ______________________________________                                         Wettable Powders                                                                             25-90      0-74     1-10                                         Oil Suspensions,                                                                              5-50     40-95     0-15                                         Emulsions, Solutions,                                                          (including Emulsifiable                                                        Concentrates)                                                                  Dusts          1-25     70-99     0-5                                          Granules and Pellets                                                                         0.01-99      5-99.99                                                                               0-15                                         High Strength 90-99     0-10      0-2                                          Compositions                                                                   ______________________________________                                    

Typical solid diluents are described in Watkins, et al., Handbook of Insecticide Dust Diluents and Carriers, 2nd Ed., Dorland Books, Caldwell, N.J. Typical liquid diluents and solvents are described in Marsden, Solvents Guide, 2nd Ed., Interscience, New York, 1950. McCutcheon's Detergents and Emulsifiers Annual, Allured Publ. Corp., Ridgewood, N.J., as well as Sisely and Wood, Encyclopedia of Surface Active Agents, Chemical Publ. Co., Inc., New York, 1964, list surfactants and recommended uses. All formulations can contain minor amounts of additives to reduce foam, caking, corrosion, microbiological growth, etc.

Solutions are prepared by simply mixing the ingredients. Fine solid compositions are made by blending and, usually, grinding as in a hammer mill or fluid energy mill. Water-dispersible granules can be produced be agglomerating a fine powder composition; see for example, Cross et al., Pesticide Formulations, Washington, D.C., 1988, pp 251-259. Suspensions are prepared by wet-milling; see, for example, U.S. Pat. No. 3,060,084. Granules and pellets can be made by spraying the active material upon preformed granular carriers or by agglomeration techniques. See Browning, "Agglomeration" Chemical Engineering, December 4, 1967, pp 147-48, Perry's Chemical Engineer's Handbook, 4th Ed., McGraw-Hill, New York, 1963, pages 8-57 and following, and WO 91/13546. Pellets can be prepared as described in U.S. Pat. No. 4,172,714. Water-dispersible and water-soluble granules can also be prepared as taught in DE 3,246,493.

For further information regarding the art of formulation, see U.S. Pat. No. 3,235,361, Col. 6, line 16 through Col. 7, line 19 and Examples 10-41; U.S. Pat. No. 3,309,192, Col. 5, line 43 through Col. 7, line 62 and Examples 8, 12, 15, 39, 41, 52, 53, 58, 132, 138-140, 162-164, 166, 167 and 169-182; U.S. 2,891,855, Col. 3, line 66 through Col. 5, line 17 and Examples 1-4; Klingman, Weed Control as a Science, John Wiley and Sons, Inc., New York, 1961, pp 81-96; and Hance et al., Weed Control Handbook, 8th Ed., Blackwell Scientific Publications, Oxford, 1989.

In the following Examples, all percentages are by weight and all formulations are worked up in conventional ways. Compound numbers refer to compounds in Table IV.

Example A

    ______________________________________                                         High Strength Concentrate                                                      ______________________________________                                         Compound 1           98.5%                                                     silica aerogel       0.5%                                                      synthetic amorphous fine silica                                                                     1.0%                                                      ______________________________________                                    

Example B

    ______________________________________                                         Wettable Powder                                                                ______________________________________                                         Compound 1               65.0%                                                 dodecylphenol polyethylene glycol ether                                                                 2.0%                                                  sodium ligninsulfonate   4.0%                                                  sodium silicoaluminate   6.0%                                                  montmorillonite (calcined)                                                                              23.0%                                                 ______________________________________                                    

Example C

    ______________________________________                                         Granule                                                                        ______________________________________                                         Compound 1            10.0%                                                    attapulgite granules (low volative                                                                   90.0%                                                    matter, 0.71/0.30 mm; U.S.S. No.                                               25-50 sieves)                                                                  ______________________________________                                    

Example D

    ______________________________________                                         Extruded Pellet                                                                ______________________________________                                         Compound 1            25.0%                                                    anhydrous sodium sulfate                                                                             10.0%                                                    crude calcium ligninsulfonate                                                                        5.0%                                                     sodium alkylnaphthalenesulfonate                                                                     1.0%                                                     calcium/magnesium bentonite                                                                          59.0%                                                    ______________________________________                                    

UTILITY

The compounds of the present invention are active postemergence and preemergence herbicides and especially for broadleaf and grass weed control in plantation crops including citrus, sugarcane, coffee, oil palm, rubber, pineapple, grapes, banana and conifers, such as loblolly pine. Most of the plantation crops are very important in mankind's diet while others are sources of useful raw materials. The compounds can be applied as preemergence or postemergence treatments using techniques of banding, directed sprays or broadcast applications. By selecting effective application rates, application techniques and adjuvants, compounds of this invention can be used for selective weed control in plantation crops.

Alternatively, compounds of this invention can be used in areas where complete control of all vegetation is desired, such as around fuel storage tanks, ammunition depots, industrial storage areas, oil well sites, drive-in theaters, around billboards, highways and railroad structures and in fence rows.

Effective application rates for the compounds of this invention are 5 to 5000 g/ha with a preferred rate range of 10 to 2000 g/ha. One skilled in the art can select the effective rates for a given situation.

The compounds of this invention may be used alone or in combination with other commercial herbicides, insecticides or fungicides. The following list exemplifies some of the herbicides suitable for use in mixtures. A combination of a compound from this invention with one or more of the following herbicides may be particularly useful for weed control in plantation crops.

Compounds of this invention can be used alone or in combination with other commercial herbicides, insecticides or fungicides. A mixture of one or more of the following herbicides with a compound of this invention may be particularly useful for weed control. Examples of other herbicides with which compounds of this invention can be formulated are: acetochlor, acifluorfen, acrolein, 2-propenal, alachlor, ametryn, amidosulfuron, ammonium sulfamate, amitrole, anilofos, asulam, atrazine, barban, benefin, bensulfuron methyl, bensulide, bentazon, benzofluor, benzoylprop, bifenox, bromacil, bromoxynil, bromoxynil heptanoate, bromoxynil octanoate, butachlor, buthidazole, butralin, butylate, cacodylic acid, 2-chloro-N,N-di-2-propenylacetamide, 2-chloroallyl diethyldithiocarbamate, chloramben, chlorbromuron, chloridazon, chlorimuron ethyl, chlormethoxynil, chlornitrofen, chloroxuron, chlorpropham, chlorsulfuron, chlortoluron, cinmethylin, cinosulfuron, clethodim, clomazone, cloproxydim, clopyralid, calcium salt of methylarsonic acid, cyanazine, cycloate, cycluron, cyperquat, cyprazine, cyprazole, cypromid, dalapon, dazomet, dimethyl 2,3,5,6-tetrachloro-1,4-benzenedicarboxylate, desmedipham, desmetryn, dicamba, dichlobenil, dichlorprop, diclofop, diethatyl, difenzoquat, diflufenican, dimepiperate, dinitramine, dinoseb, diphenamid, dipropetryn, diquat, diuron, 2-methyl-4,6-dinitrophenol, disodium salt of methylarsonic acid, dymron, endothall, S-ethyl dipropylcarbamothioate, esprocarb, ethalfluralin, ethametsulfuron methyl, ethofumesate, fenac, fenoxaprop, fenuron, salt of fenuron and trichloroacetic acid, flamprop, fluazifop, fluazifop-P, fluchloralin, flumesulam, flumipropyn, fluometuron, fluorochloridone, fluorodifen, fluoroglycofen, flupoxam, fluridone, fluroxypyr, fluzasulfuron, fomesafen, fosamine, glyphosate, haloxyfop, hexaflurate, hexazinone, imazamethabenz, imazapyr, imazaquin, imazamethabenz methyl, imazethapyr, imazosulfuron, ioxynil, isopropalin, isoproturon, isouron, isoxaben, karbutilate, lactofen, lenacil, linuron, metobenzuron, metsulfuron methyl, methylarsonic acid, monoammonium salt of methylarsonic acid, (4-chloro-2-methylphenoxy)acetic acid, S,S'-dimethyl-2-(difluoromethyl)-4-(2-methylpropyl)-6-(trifluoromethyl)-3,5-pyridinedicarbothioate, mecoprop, mefenacet, mefluidide, methalpropalin, methabenzthiazuron, metham, methazole, methoxuron, metolachlor, metribuzin, 1,2-dihydropyridazine-3,6-dione, molinate, monolinuron, monuron, monuron salt and trichloroacetic acid, monosodium salt of methylarsonic acid, napropamide, naptalam, neburon, nicosulfuron, nittalin, nitrofen, nitrofluorfen, norea, norflurazon, oryzalin, oxadiazon, oxyfluorfen, paraquat, pebulate, pendimethalin, perfluidone, phenmedipham, picloram, 5-[2-chloro-4-(trifluoromethyl)phenoxy]-2-nitroacetophenone oxime-O-acetic acid methyl ester, pretilachlor, primisulfuron, procyazine, profluralin, prometon, prometryn, pronamide, propachlor, propanil, propazine, propham, prosulfalin, prynachlor, pyrazolate, pyrazon, pyrazosulfuron ethyl, quinchlorac, quizalofop ethyl, rimsulfuron, secbumeton, sethoxydim, siduron, simazine, 1-(a,a-dimethylbenzyl)-3-(4-methylphenyl)urea, sulfometuron methyl, trichloroacetic acid, tebuthiuron, terbacil, terbuchlor, terbuthylazine, terbutol, terbutryn, thifensulfuron methyl, thiobencarb, triallate, trialkoxydim, triasulfuron, tribenuron methyl, triclopyr, tridiphane, trifluralin, trimeturon, (2,4-dichlorophenoxy)acetic acid, 4-(2,4-dichlorophenoxy)butanoic acid, vernolate, and xylachlor.

In certain instances, combinations with other herbicides having a similiar spectrum of control but a different mode of action will be particularly advantageous for resistance management.

A herbicidally effective amount of. the compounds of this invention is determined by a number of factors. These factors include: formulation selected, method of application, amount and type of vegetation present, growing conditions, etc. In general, a herbicidally effective amount of a compound(s) of this invention is applied at rates from about 0.001 to 20 kg/ha with a preferred rate range of 0.004 to 0.25 kg/ha. One skilled in the art can easily determine application rates necessary for the desired level of weed control.

The following Tests demonstrate the control efficacy of the compounds of this invention specific weeds. The weed control afforded by the compounds is not limited, however, to these species. See Index Tables IV through VI for compound descriptions.

Selective herbicidal properties of the subject compounds were discovered in greenhouse tests as described below. Test procedures and results follows.

                                      TABLE IV                                     __________________________________________________________________________      ##STR21##                                                                     No.                                                                               R.sup.1 R.sup.2 R.sup.3                                                                           X Y m.p. (°C.)                                                                    .sup.1 H-NMR                                   __________________________________________________________________________     1  CH.sub.3                                                                               CH.sub.2 Ph                                                                            CF.sub.3                                                                          Cl                                                                               F 145-147                                                                              7.4(m, 6H)                                                                     6.85(d, 1H)                                                                    6.4(s, 1H)                                                                     5.1(s, 2H)                                                                     3.55(s, 3H)                                    2  CH.sub.3                                                                               H       CF.sub.3                                                                          Cl                                                                               F Foam  7.15(d, 1H)                                                                    6.9(d, 1H)                                                                     6.4(s, 1H)                                                                     5.8(s, 1H)                                                                     3.6(s, 3H)                                     3  CH.sub.3                                                                               CH.sub.2 CCH                                                                           CF.sub.3                                                                          Cl                                                                               F Foam  7.35(d, 1H)                                                                    7.0(d, 1H)                                                                     6.4(s, 1H)                                                                     4.78(d, 2H)                                                                    3.58(s, 3H)                                                                    2.6(d, 1H)                                     4  CH.sub.2 CCH                                                                           CH.sub.2 CCH                                                                           CF.sub.3                                                                          Cl                                                                               F Oil   7.35(d, 1H)                                                                    7.0(d, 1H)                                                                     6.4(s, 1H)                                                                     4.75(m, 4H)                                                                    2.6(m, 1H)                                                                     2.4(m, 1H)                                     7  CH.sub.2 CHCH.sub.2                                                                    CH.sub.2 CHCH.sub.2                                                                    CF.sub.3                                                                          Cl                                                                               F Oil   7.3(d, 1H)                                                                     6.8(d, 1H)                                                                     6.4(s, 1H)                                                                     6.0(m, 2H)                                                                     5.4(m, 4H)                                                                     4.6(d, 4H)                                     9  CH.sub.3                                                                               CH.sub.2 CHCH.sub.2                                                                    CF.sub.3                                                                          Cl                                                                               F 102-105                                                                              7.3(d, 1H)                                                                     6.8(d, 1H)                                                                     6.4(s, 1H)                                                                     6.0(m, 1H)                                                                     5.4(m, 2H)                                                                     4.6(d, 2H)                                                                     3.6(s, 3H)                                     __________________________________________________________________________

                                      TABLE V                                      __________________________________________________________________________      ##STR22##                                                                                                m.p.                                                No.                                                                               R.sup.1                                                                               R.sup.3                                                                           R.sup.4                                                                          R.sup.9 X Y (°C.)                                                                        .sup.1 H-NMR                                   __________________________________________________________________________     11 CH.sub.3                                                                              CF.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               F Foam 7.05 (d, 1H)                                                                   6.4 (s, 1H)                                                                    5.1 (m, 1H)                                                                    3.55 (s, 3H)                                                                   3.1 (m, 1H)                                                                    2.8 (m, 1H)                                                                    1.5 (d, 3H)                                    12 CH.sub.3                                                                              CF.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               Cl                                                                               64-66                                                                               7.3 (s, 1H)                                                                    6.4 (s, 1H)                                                                    5.1 (m, 1H)                                                                    3.6 (d, 3H)                                                                    3.25 (m, 1H)                                                                   2.75 (m, 1H)                                                                   1.54 (d, d 3H)                                 13 CH.sub.2 CCH                                                                          CF.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               F Oil  7.05 (d, 1H)                                                                   6.4 (s, 1H)                                                                    5.1 (m, 1H)                                                                    4.7 (d, 2H)                                                                    3.2 (m, 1H)                                                                    2.8 (m, 1H)                                                                    2.4 (s, 1H)                                                                    1.5 (s, 3H)                                    14 CH.sub.2 CH.sub.2 CH.sub.2                                                            CF.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               F Oil  7.05 (d, 1H)                                                                   6.4 (s, 1H)                                                                    5.9 (m, 1H)                                                                    5.3 (m, 2H)                                                                    5.1 (m, 1H)                                                                    4.6 (d, 1H)                                                                    3.2 (m, 1H)                                                                    2.8 (m, 1H)                                                                    1.5 (d, 3H)                                    15 CH.sub.2 Ph                                                                           CF.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               F Oil  7.2 (m, 7H)                                                                    7.0 (d, 1H)                                                                    6.4 (s, 1H)                                                                    5.2 (d, 2H)                                                                    5.1 (m, 1H)                                                                    3.1 (m, 1H)                                                                    2.7 (m, 1H)                                                                    1.5 (d, 3H)                                    17 CH.sub.3                                                                              CH.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               F Oil  7.0 (d, 1H)                                                                    5.7 (s, 1H)                                                                    5.0 (m, 1H)                                                                    3.4 (s, 3H)                                                                    3.2 (d, d 1H)                                                                  2.8 (d, d 1H)                                                                  2.3 (s, 3H)                                                                    1.5 (d, 3H)                                    19 CH.sub.2 CH.sub.3                                                                     CH.sub.3                                                                          H CH.sub.3                                                                               Cl                                                                               F 140-142                                                                             7.0 (d, 1H)                                                                    5.68 (s, 1H)                                                                   5.05 (m, 1H)                                                                   3.95 (q, 1H)                                                                   3.2 (qu, 1H)                                                                   2.8 (qu, 1H)                                                                   2.35 (s, 3H)                                                                   1.55 (d, 3H)                                                                   1.3 (t, 3H)                                    20 CH.sub.3                                                                              CF.sub.3                                                                          H CO.sub.2 H                                                                             Cl                                                                               F 190-194                                             21 CH.sub.3                                                                              CF.sub.3                                                                          H CO.sub.2 tBu                                                                           Cl                                                                               F 65-67                                               22 CH.sub.3                                                                              CF.sub.3                                                                          H CO.sub.2 CH.sub.3                                                                      Cl                                                                               F 77-79                                               23 CH.sub.3                                                                              CF.sub.3                                                                          H CO.sub.2 iPr                                                                           Cl                                                                               F 56-59                                               24 CH.sub.3                                                                              CF.sub.3                                                                          H CON(CH.sub.3).sub.2                                                                    Cl                                                                               F 92-94                                               25 CH.sub.3                                                                              CF.sub.3                                                                          H CH.sub.2 OC(O)CH.sub.3                                                                 Cl                                                                               F 58-61                                               __________________________________________________________________________

                                      TABLE VI                                     __________________________________________________________________________      ##STR23##                                                                                             m.p.                                                   No.                                                                               R.sup.1                                                                           R.sup.3                                                                             X Y R.sup.2  (°C.)                                                                        .sup.1 H-NMR                                      __________________________________________________________________________     5  CH.sub.3                                                                          N(CH.sub.3).sub.2                                                                   Cl                                                                               F H        247-249                                                                             7.45 (d, 1H)                                                                   6.95 (d, 1H)                                                                   3.3 (s, 3H)                                                                    3.0 (s, 6H)                                       6  CH.sub.3                                                                          N(CH.sub.3).sub.2                                                                   Cl                                                                               F CH.sub.2 Ph                                                                             193-194                                                                             7.4 (m, 6H)                                                                    6.95 (d, 1 H)                                                                  5.05 (d, 2H)                                                                   3.45 (s, 3H)                                                                   3.1 (s, 6H)                                       8  CH.sub.3                                                                          N(CH.sub.3).sub.2                                                                   Cl                                                                               F CH.sub.2 CCH                                                                             61-65                                                                              7.0 (d, 1H)                                                                    4.75 (m, 2H)                                                                   3.45 (s, 3H)                                                                   3.1 (s, 6H)                                                                    2.6 (m, 1H)                                       16 CH.sub.3                                                                          N(CH.sub.3).sub.2                                                                   Cl                                                                               F H        134-135                                                                             7.28 (s, 1H)                                                                   6.84 (d, 1H)                                                                   6.05 (m, 1H)                                                                   5.45 (d, 1H)                                                                   5.3 (d, 1H)                                                                    4.55 (s, 2H)                                                                   3.45 (s, 3H)                                                                   3.12 (s, 6H)                                      18 CH.sub.3                                                                          N(CH.sub.3).sub.2                                                                   Cl                                                                               F CH(CH.sub.3)CH.sub.2                                                                    191-195                                                                             7.3 (d, 1H)                                                                    6.8 (d, 1H)                                                                    6.36 (s, 1H)                                                                   6.0 (m, 1H)                                                                    5.4 (m, 2H)                                                                    4.55 (d, 2H)                                                                   3.56 (s, 3H)                                      __________________________________________________________________________

TEST A

Seeds of barley (Hordeum vulgate), barnyardgrass (Echinochloa crus-galli), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), cheatgrass (Bromus secalinus), chickweed (Stellaria media), cocklebur (Xanthium pensylvanicum), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria spp.), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), rape (Brassica napus), rice (Oryza satira), sorghum (Sorghum bicolor), soybean (Glycine max), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygonurn convolvulus), and wild oat (Avena fatua) and purple nutsedge (Cyperus rotundus) tubers were planted and treated preemergence with test chemicals dissolved in a non-phytotoxic solvent. At the same time, these crop and weed species were also treated with postemergence applications of test chemicals. Plants ranged in height from two to eighteen cm (one to four leaf stage) for postemergence treatments. Treated plants and controls were maintained in a greenhouse for twelve to sixteen days, after which all species were compared to controls and visually evaluated. Plant response ratings, summarized in Table A, are based on a scale of 0 to 10 where 0 is no effect and 10 is complete control. A dash (--) response indicates no test result.

                                      TABLE A                                      __________________________________________________________________________                 COMPOUND                                                           Rate 400 g/ha                                                                              1  2 3  5 6  8 11 16 17 18                                         __________________________________________________________________________     POSTEMERGENCE                                                                  Barley      6  9 10 3 5  6 10 -- 6  8                                          Barnyardgrass                                                                              9  10                                                                               10 5 3  10                                                                               10 7  9  10                                         Bedstraw    10 10                                                                               10 3 4  8 10 -- 8  10                                         Blackgrass  10 9 10 3 4  5 10 -- 5  9                                          Cheatgrass  7  8 10 4 4  5 10 -- 5  10                                         Chickweed   10 10                                                                               10 3 4  8 10 -- 5  10                                         Cocklebur   10 10                                                                               10 3 6  8 10 8  7  9                                          Corn        6  9 10 2 3  10                                                                               10 3  6  9                                          Cotton      10 10                                                                               10 9 9  10                                                                               10 10 10 10                                         Crabgrass   5  7 10 3 4  10                                                                               10 5  9  9                                          Giant foxtail                                                                              8  10                                                                               10 3 6  9 10 9  9  10                                         Lambsquarter                                                                               10 10                                                                               10 5 8  10                                                                               10 -- 10 10                                         Morningglory                                                                               10 10                                                                               10 8 7  9 10 10 9  10                                         Nutsedge    5  --                                                                               -- 1 0  9 7  2  2  5                                          Rape        10 7 10 1 5  9 10 -- 7  10                                         Rice        6  7 10 3 3  9 10 7  9  9                                          Sorghum     6  9 10 2 3  6 10 4  9  10                                         Soybean     10 10                                                                               10 4 6  9 10 9  9  9                                          Sugar beet  10 10                                                                               10 5 9  10                                                                               10 -- 10 10                                         Velvetleaf  10 10                                                                               10 2 9  10                                                                               10 10 10 10                                         Wheat       5  --                                                                               -- 3 4  6 10 -- 7  10                                         Wild buckwheat                                                                             -- --                                                                               -- 6 6  10                                                                               10 -- 10 10                                         Wild oat    9  9 10 2 4  6 10 -- 8  10                                         __________________________________________________________________________                 COMPOUND                                                           Rate 400 g/ha                                                                              1  2 3  5 6  8 11 16 17 18                                         __________________________________________________________________________     PREEMERGENCE                                                                   Barley      3  3 9  0 0  8 9  -- 4  5                                          Barnyardgrass                                                                              9  9 10 0 0  9 10 9  10 10                                         Bedstraw    10 10                                                                               10 3 10 10                                                                               10 -- 10 9                                          Blackgrass  10 7 10 0 5  9 10 -- 4  10                                         Cheatgrass  10 10                                                                               10 0 0  9 10 -- 9  10                                         Chickweed   10 9 10 0 3  10                                                                               10 -- 4  9                                          Cocklebur   0  7 10 0 0  10                                                                               10 6  6  10                                         Corn        3  4 10 0 0  6 10 8  8  10                                         Cotton      8  8 10 0 0  10                                                                               10 6  8  10                                         Crabgrass   10 9 10 0 9  10                                                                               10 10 10 10                                         Giant foxtail                                                                              10 10                                                                               10 0 9  10                                                                               10 10 10 10                                         Lambsquarter                                                                               10 10                                                                               10 0 10 10                                                                               10 -- 10 10                                         Morningglory                                                                               5  10                                                                               10 0 0  10                                                                               10 10 9  10                                         Nutsedge    2  10                                                                               10 0 10 1 7  3  4  5                                          Rape        10 10                                                                               10 1 2  10                                                                               10 -- 10 10                                         Rice        5  3 10 0 0  10                                                                               10 6  9  10                                         Sorghum     7  9 10 0 0  4 10 8  9  10                                         Soybean     3  9 10 0 0  6 10 4  9  9                                          Sugar beet  10 10                                                                               10 1 9  10                                                                               10 -- 10 10                                         Velvetleaf  10 10                                                                               10 0 10 10                                                                               10 10 10 10                                         Wheat       3  7 10 0 0  9 9  -- 6  8                                          Wild buckwheat                                                                             10 10                                                                               10 0 10 10                                                                               10 -- 10 10                                         Wild oat    9  9 10 0 0  10                                                                               10 -- 3  10                                         __________________________________________________________________________                COMPOUND           COMPOUND                                         Rate 200 g/ha                                                                             4  9 12 Rate 200 g/ha                                                                             4  9 12                                          __________________________________________________________________________     POSTEMERGENCE      PREEMERGENCE                                                Barley     5  7 7  Barley     2  6 1                                           Barnyardgrass                                                                             10 10                                                                               6  Barnyardgrass                                                                             10 10                                                                               9                                           Bedstraw   9  10                                                                               9  Bedstraw   9  10                                                                               10                                          Blackgrass 6  9 4  Blackgrass 9  10                                                                               8                                           Cheatgrass 7  9 5  Cheatgrass 9  10                                                                               3                                           Chickweed  10 10                                                                               6  Chickweed  10 10                                                                               1                                           Cocklebur  7  10                                                                               7  Cocklebur  6  10                                                                               7                                           Corn       9  9 7  Corn       9  9 9                                           Cotton     10 10                                                                               10 Cotton     7  9 3                                           Crabgrass  9  10                                                                               7  Crabgrass  10 10                                                                               10                                          Giant foxtail                                                                             9  10                                                                               8  Giant foxtail                                                                             10 10                                                                               10                                          Lambsquarter                                                                              10 10                                                                               10 Lambsquarter                                                                              10 10                                                                               10                                          Morningglory                                                                              9  10                                                                               9  Morningglory                                                                              10 10                                                                               10                                          Nutsedge   5  5 1  Nutsedge   10 2 0                                           Rape       10 10                                                                               9  Rape       8  10                                                                               10                                          Rice       10 9 9  Rice       9  9 8                                           Sorghum    9  9 9  Sorghum    9  10                                                                               7                                           Soybean    9  9 10 Soybean    9  10                                                                               8                                           Sugar beet 10 10                                                                               10 Sugar beet 9  10                                                                               10                                          Velvetleaf 10 10                                                                               8  Velvetleaf 10 10                                                                               10                                          Wheat      7  6 7  Wheat      7  9 2                                           Wild buckwheat                                                                            10 10                                                                               10 Wild buckwheat                                                                            10 10                                                                               10                                          Wild oat   9  10                                                                               8  Wild oat   8  10                                                                               6                                           __________________________________________________________________________                 COMPOUND                                                           Rate 100 g/ha                                                                              1  2 3  5 6  8 11 16 17 18                                         __________________________________________________________________________     POSTEMERGENCE                                                                  Barley      5  5 7  3 3  5 7  -- 4  7                                          Barnyardgrass                                                                              8  7 10 1 2  4 10 3  8  9                                          Bedstraw    8  9 10 2 3  5 10 -- 7  9                                          Blackgrass  6  5 10 2 2  5 10 -- 4  6                                          Cheatgrass  6  5 9  1 3  4 10 -- 3  5                                          Chickweed   -- --                                                                               10 2 2  6 10 -- 4  8                                          Cocklebur   8  6 10 2 4  6 10 7  6  8                                          Corn        5  3 9  2 2  7 9  3  4  6                                          Cotton      10 10                                                                               10 9 10 10                                                                               10 10 10 10                                         Crabgrass   4  2 10 2 -- 7 10 2  5  8                                          Giant foxtail                                                                              5  9 10 2 5  7 10 4  7  8                                          Lambsquarter                                                                               10 10                                                                               10 3 7  9 10 -- 10 10                                         Morningglory                                                                               10 10                                                                               10 5 7  9 10 8  8  10                                         Nutsedge    5  2 -- 0 0  --                                                                               8  0  2  3                                          Rape        10 3 10 1 2  7 10 -- 5  9                                          Rice        5  6 9  3 3  6 10 4  9  8                                          Sorghum     5  4 9  1 2  5 10 4  5  8                                          Soybean     8  8 10 3 5  8 9  8  9  9                                          Sugar beet  10 10                                                                               10 3 7  10                                                                               10 -- 9  10                                         Velvetleaf  10 10                                                                               10 2 6  7 10 10 9  10                                         Wheat       4  4 9  3 2  4 8  -- 5  9                                          Wild buckwheat                                                                             -- --                                                                               10 3 3  10                                                                               10 -- 9  9                                          Wild oat    7  5 9  3 3  4 9  -- 6  9                                          __________________________________________________________________________                 COMPOUND                                                           Rate 100 g/ha                                                                              1  2 3  5 6  8 11 16 17 18                                         __________________________________________________________________________     PREEMERGENCE                                                                   Barley      0  0 4  0 0  1 8  -- 0  2                                          Barnyardgrass                                                                              8  3 10 0 0  3 10 2  8  9                                          Bedstraw    10 5 10 0 0  2 10 -- 4  8                                          Blackgrass  9  3 10 0 0  5 10 -- 2  6                                          Cheatgrass  5  2 8  0 0  4 10 -- 1  8                                          Chickweed   10 --                                                                               10 0 2  5 10 -- 2  9                                          Cocklebur   0  0 10 0 0  2 10 2  2  5                                          Corn        3  0 9  0 0  0 9  1  2  7                                          Cotton      0  0 10 0 0  1 10 2  4  10                                         Crabgrass   9  6 10 0 9  10                                                                               10 2  9  9                                          Giant foxtail                                                                              9  10                                                                               10 0 0  2 10 5  5  10                                         Lambsquarter                                                                               10 10                                                                               10 0 10 10                                                                               10 -- 10 9                                          Morningglory                                                                               0  2 10 0 0  3 10 6  4  10                                         Nutsedge    0  8 7  0 0  0 5  2  1  4                                          Rape        10 3 10 0 0  9 10 -- 6  9                                          Rice        1  1 9  0 0  6 9  3  4  8                                          Sorghum     3  1 9  0 0  3 10 1  1  6                                          Soybean     1  2 9  0 0  2 10 1  8  5                                          Sugar beet  5  7 10 0 0  7 10 -- 9  9                                          Velvetleaf  2  10                                                                               10 0 0  10                                                                               10 6  10 10                                         Wheat       0  1 8  0 0  1 7  -- 0  4                                          Wild buckwheat                                                                             10 0 10 0 0  8 10 -- 10 9                                          Wild oat    7  3 9  0 0  0 9  -- 0  5                                          __________________________________________________________________________                COMPOUND           COMPOUND                                         Rate 50 g/ha                                                                              4  9 12 Rate 50 g/ha                                                                              4  9 12                                          __________________________________________________________________________     POSTEMERGENCE      PREEMERGENCE                                                Barley     4  5 5  Barley     0  2 0                                           Barnyardgrass                                                                             7  9 4  Barnyardgrass                                                                             7  9 7                                           Bedstraw   9  10                                                                               6  Bedstraw   10 10                                                                               8                                           Blackgrass 4  6 2  Blackgrass 5  9 5                                           Cheatgrass 5  6 3  Cheatgrass 5  8 2                                           Chickweed  10 10                                                                               3  Chickweed  10 10                                                                               0                                           Cocklebur  6  10                                                                               4  Cocklebur  0  9 0                                           Corn       5  7 4  Corn       5  9 6                                           Cotton     9  10                                                                               9  Cotton     2  7 2                                           Crabgrass  6  9 5  Crabgrass  9  10                                                                               10                                          Giant foxtail                                                                             7  9 7  Giant foxtail                                                                             8  10                                                                               9                                           Lambsquarter                                                                              10 10                                                                               9  Lambsquarter                                                                              10 10                                                                               10                                          Morningglory                                                                              8  10                                                                               6  Morningglory                                                                              2  10                                                                               5                                           Nutsedge   5  3 1  Nutsedge   5  3 0                                           Rape       10 10                                                                               5  Rape       2  10                                                                               7                                           Rice       8  8 7  Rice       2  9 7                                           Sorghum    7  8 5  Sorghum    3  9 6                                           Soybean    9  9 6  Soybean    2  10                                                                               5                                           Sugar beet 10 10                                                                               9  Sugar beet 9  10                                                                               10                                          Velvetleaf 8  10                                                                               5  Velvetleaf 9  10                                                                               9                                           Wheat      5  7 3  Wheat      0  7 1                                           Wild buckwheat                                                                            10 10                                                                               9  Wild buckwheat                                                                            9  10                                                                               5                                           Wild oat   5  7 4  Wild oat   5  8 1                                           __________________________________________________________________________

TEST B

The compounds evaluated in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application), to water that covered the soil surface (flood application), and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence and postemergence tests, while a silt loam soil was used in the flood test. Water depth was approximately 2.5 cm for the flood test and was maintained at this level for the duration of the test.

Plant species in the preemergence and postemergence tests consisted of barley (Hordeurn vulgare), bedstraw (Galium aparine), blackgrass (Alopecurus myosuroides), chickweed (Stellaria media), corn (Zea mays), cotton (Gossypium hirsutum), crabgrass (Digitaria sanguinalis), downy brome (Bromus rectorurn), giant foxtail (Setaria faberii), lambsquarters (Chenopodium album), morningglory (Ipomoea hederacea), pigweed (Amaranthusretroflexus), rape (Brassica napus), ryegrass (Lolium multifiorum), sorghum (Sorghum bicolor), soybean (Glycine max), speedwell (Veronica persica), sugar beet (Beta vulgaris), velvetleaf (Abutilon theophrasti), wheat (Triticum aestivum), wild buckwheat (Polygon urn convolvulus), and wild oat (Avena fatua).

All plant species were planted one day before application of the compound for the preemergence portion of this test. Plantings of these species were adjusted to produce plants of appropriate size for the post-emergence portion of the test. Plant species in the flood test consisted of barnyardgrass (Echinochloa crus-galli), rice (Oryza sativa), umbrella sedge

(Cyperus difformis) and duck salad (Heteranthera limosa). All plant species were grown using normal greenhouse practices. Visual evaluations of injury expressed on treated,plants, when compared to untreated controls, were recorded approximately fourteen to twenty one days after application of the test compound. Plant response ratings, summarized in Table B, were recorded on a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash (--) response indicates no test result.

                                      TABLE B                                      __________________________________________________________________________                COMPOUND                 COMPOUND                                   Rate 250 g/ha                                                                             4             Rate 250 g/ha                                                                             4                                          __________________________________________________________________________     POSTEMERGENCE            PREEMERGENCE                                          Barley Igri                                                                               70            Barley Igri                                                                               50                                         Barnyard 2 leaf                                                                           --            Bedstraw   100                                        Barnyardgrass                                                                             100           Blackgrass 100                                        Bedstraw   100           Chickweed  100                                        Blackgrass 100           Corn       100                                        Chickweed  100           Cotton     100                                        Corn       90            Crabgrass  100                                        Cotton     100           Downy Brome                                                                               95                                         Crabgrass  100           Giant foxtail                                                                             100                                        Downy Brome                                                                               100           Lambsquarters                                                                             100                                        Duck salad 15            Morningglory                                                                              100                                        Giant foxtail                                                                             100           Pigweed    100                                        Lambsquarters                                                                             100           Rape       100                                        Morningglory                                                                              100           Ryegrass   100                                        Pigweed    100           Sorghum    100                                        Rape       100           Soybean    100                                        Rice Japonica                                                                             100           Speedwell  --                                         Ryegrass   90            Sugar beet 100                                        Sorghum    100           Velvetleaf 100                                        Soybean    100           Wheat      90                                         Speedwell  --            Wild buckwheat                                                                            100                                        Sugar beet 100           Wild oat   95                                         Umbrella sedge                                                                            10                                                                  Velvetleaf 100                                                                 Wheat      90                                                                  Wild buckwheat                                                                            100                                                                 Wild oat   90                                                                  __________________________________________________________________________                COMPOUND                  COMPOUND                                  Rate 125 g/ha                                                                             1  3  4  9  12 Rate 125 g/ha                                                                             1  3  4  12                               __________________________________________________________________________     POSTEMERGENCE             PREEMERGENCE                                         Barley Igri                                                                               0  100                                                                               60 95 -- Barley Igri                                                                               0  100                                                                               30 50                               Barnyard 2 leaf                                                                           -- -- -- -- -- Bedstraw   100                                                                               100                                                                               100                                                                               100                              Barnyardgrass                                                                             100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               Blackgrass 30 100                                                                               90 90                               Bedstraw   100                                                                               100                                                                               100                                                                               100                                                                               -- Chickweed  100                                                                               100                                                                               100                                                                               0                                Blackgrass 50 100                                                                               100                                                                               100                                                                               -- Corn       50 100                                                                               70 90                               Chickweed  100                                                                               100                                                                               100                                                                               100                                                                               -- Cotton     70 100                                                                               100                                                                               10                               Corn       25 98 90 98 -- Crabgrass  100                                                                               100                                                                               100                                                                               100                              Cotton     100                                                                               100                                                                               100                                                                               100                                                                               -- Downy Brome                                                                               0  100                                                                               90 50                               Crabgrass  50 100                                                                               95 100                                                                               -- Giant foxtail                                                                             100                                                                               100                                                                               100                                                                               100                              Downy Brome                                                                               0  100                                                                               85 100                                                                               -- Lambsquarters                                                                             100                                                                               100                                                                               100                                                                               100                              Duck salad 0  90 0  95 30 Morningglory                                                                              100                                                                               100                                                                               100                                                                               100                              Giant foxtail                                                                             100                                                                               100                                                                               100                                                                               100                                                                               -- Pigweed    100                                                                               100                                                                               100                                                                               100                              Lambsquarters                                                                             100                                                                               100                                                                               100                                                                               100                                                                               -- Rape       100                                                                               100                                                                               100                                                                               100                              Morningglory                                                                              100                                                                               100                                                                               100                                                                               100                                                                               -- Ryegrass   20 100                                                                               95 90                               Pigweed    100                                                                               100                                                                               100                                                                               100                                                                               -- Sorghum    60 100                                                                               90 100                              Rape       100                                                                               100                                                                               100                                                                               100                                                                               -- Soybean    100                                                                               100                                                                               100                                                                               100                              Rice Japonica                                                                             95 100                                                                               100                                                                               100                                                                               95 Speedwell  100                                                                               100                                                                               -- 100                              Ryegrass   40 100                                                                               70 100                                                                               -- Sugar beet 100                                                                               100                                                                               100                                                                               100                              Sorghum    60 100                                                                               90 100                                                                               -- Velvetleaf 100                                                                               100                                                                               100                                                                               100                              Soybean    98 100                                                                               90 100                                                                               -- Wheat      0  100                                                                               85 100                              Speedwell  100                                                                               100                                                                               -- 100                                                                               -- Wild buckwheat                                                                            100                                                                               100                                                                               100                                                                               100                              Sugar beet 100                                                                               100                                                                               100                                                                               100                                                                               -- Wild oat   0  100                                                                               75 90                               Umbrella sedge                                                                            100                                                                               100                                                                               0  100                                                                               85                                                      Velvetleaf 100                                                                               100                                                                               100                                                                               100                                                                               --                                                      Wheat      0  100                                                                               60 95 --                                                      Wild buckwheat                                                                            100                                                                               100                                                                               100                                                                               100                                                                               --                                                      Wild oat   40 100                                                                               80 95 --                                                      __________________________________________________________________________                COMPOUND                 COMPOUND                                   Rate 62 g/ha                                                                              1  3  4   11 Rate 62 g/ha                                                                               1  3  4   11                               __________________________________________________________________________     POSTMERGENCE            PREEMRGENCE                                            Barley Igri                                                                               0  95 50  90 Barley Igri 0  100                                                                               60  90                               Barnyard 2 leaf                                                                           -- -- 100 -- Bedstraw    100                                                                               100                                                                               100 100                              Barnyardgrass                                                                             100                                                                               100                                                                               100 100                                                                               Blackgrass  -- 100                                                                               85  100                              Bedstraw   100                                                                               100                                                                               100 100                                                                               Chickweed   100                                                                               100                                                                               100 100                              Blackgrass 50 100                                                                               95  100                                                                               Corn        0  100                                                                               70  100                              Chickweed  100                                                                               100                                                                               100 100                                                                               Cotton      0  98 100 100                              Corn       20 98 80  100                                                                               Crabgrass   80 100                                                                               100 160                              Cotton     100                                                                               100                                                                               100 100                                                                               Downy Brome 0  100                                                                               75  100                              Crabgrass  20 100                                                                               90  100                                                                               Giant foxtail                                                                              100                                                                               100                                                                               100 100                              Downy Brome                                                                               0  100                                                                               75  90 Lambsquarters                                                                              100                                                                               100                                                                               100 100                              Duck salad 0  90 0   90 Morningglory                                                                               100                                                                               100                                                                               100 190                              Giant foxtail                                                                             80 100                                                                               95  100                                                                               Pigweed     100                                                                               100                                                                               100 100                              Lambsquarters                                                                             100                                                                               100                                                                               100 100                                                                               Rape        50 100                                                                               100 100                              Morningglory                                                                              100                                                                               100                                                                               100 100                                                                               Ryegrass    0  100                                                                               95  100                              Pigweed    100                                                                               100                                                                               100 100                                                                               Sorghum     50 100                                                                               80  100                              Rape       100                                                                               100                                                                               100 100                                                                               Soybean     30 100                                                                               70  100                              Rice Japonica                                                                             90 100                                                                               95  100                                                                               Speedwell   100                                                                               100                                                                               100 --                               Ryegrass   40 100                                                                               70  90 Sugar beet  100                                                                               100                                                                               100 100                              Sorghum    30 100                                                                               85  100                                                                               Velvetleaf  100                                                                               100                                                                               100 100                              Soybean    98 100                                                                               100 100                                                                               Wheat       0  100                                                                               100 100                              Speedwell  100                                                                               100                                                                               100 -- Wild buckwheat                                                                             100                                                                               100                                                                               100 100                              Sugar beet 100                                                                               100                                                                               100 100                                                                               Wild oat    0  100                                                                               70  100                              Umbrella sedge                                                                            90 100                                                                               0   90                                                        Velvetleaf 100                                                                               100                                                                               100 100                                                       Wheat      0  100                                                                               60  90                                                        Wild buckwheat                                                                            100                                                                               100                                                                               100 100                                                       Wild oat   40 100                                                                               60  95                                                        __________________________________________________________________________                COMPOUND                  COMPOUND                                  Rate 31 g/ha                                                                              1  2  4  9  12 Rate 31 g/ha                                                                              1  2  4  12                               __________________________________________________________________________     POSTEMERGENCE             PREEMERGENCE                                         Barley Igri                                                                               0  90 40 80 -- Barle Igri 0  90 0  20                               Barnyard 2 leaf                                                                           -- -- -- -- -- Bedstraw   100                                                                               100                                                                               100                                                                               90                               B.arnyardgrass                                                                            100                                                                               100                                                                               95 100                                                                               70 Blackgrass 0  100                                                                               70 40                               Bedstraw   100                                                                               100                                                                               100                                                                               100                                                                               -- Chickweed  100                                                                               100                                                                               100                                                                               0                                Blackgrass 30 100                                                                               60 80 -- Corn       0  100                                                                               40 60                               Chickweed  90 100                                                                               100                                                                               100                                                                               -- Cotton     0  98 20 0                                Corn       20 70 60 90 -- Crabgras3  80 100                                                                               100                                                                               98                               Cotton     100                                                                               100                                                                               100                                                                               100                                                                               -- Downy Brome                                                                               0  100                                                                               40 20                               Crabgrass  0  100                                                                               70 90 -- Giant foxtail                                                                             80 100                                                                               95 100                              Downy Brome                                                                               0  100                                                                               50 80 -- Lambsquarters                                                                             100                                                                               100                                                                               100                                                                               100                              Duck salad 0  75 0  95 0  Morningglory                                                                              30 100                                                                               100                                                                               50                               Giant foxtail                                                                             20 100                                                                               75 98 -- Pigweed    100                                                                               100                                                                               100                                                                               100                              Lambsquarters                                                                             100                                                                               100                                                                               100                                                                               100                                                                               -- Rape       20 100                                                                               40 50                               Morningglory                                                                              100                                                                               100                                                                               90 100                                                                               -- Ryegrass   0  100                                                                               80 50                               Pigweed    100                                                                               100                                                                               100                                                                               100                                                                               -- Sorghum    30 100                                                                               70 90                               Rape       100                                                                               100                                                                               100                                                                               100                                                                               -- Soybean    20 100                                                                               70 40                               Rice Japonica                                                                             75 100                                                                               90 100                                                                               90 Speedwell  100                                                                               100                                                                               -- 100                              Ryegrass   30 100                                                                               60 95 -- Sugar beet 100                                                                               100                                                                               100                                                                               100                              Sorghum    20 100                                                                               70 95 -- Velvetleaf 100                                                                               100                                                                               100                                                                               100                              Soybean    80 100                                                                               90 100                                                                               -- Wheat      0  100                                                                               40 50                               Speedwell  100                                                                               100                                                                               -- 100                                                                               -- Wild buckwheat                                                                            100                                                                               100                                                                               100                                                                               80                               Sugar beet 100                                                                               100                                                                               100                                                                               100                                                                               -- Wild oat   0  100                                                                               30 30                               Umbrella sedge                                                                            0  85 0  100                                                                               80                                                      Velvetleaf 100                                                                               100                                                                               100                                                                               100                                                                               --                                                      Wheat      0  100                                                                               50 50 --                                                      Wild buckwheat                                                                            100                                                                               100                                                                               100                                                                               100                                                                               --                                                      Wild oat   0  100                                                                               50 50 --                                                      __________________________________________________________________________                COMPOUND                 COMPOUND                                   Rate 16 g/ha                                                                              1  3  4   11 Rate 16 g/ha                                                                               1  3  4   11                               __________________________________________________________________________     POSTEMERGENCE           PREEMERGENCE                                           Barley Igri                                                                               0  30 30  70 Barley Igri 0  50 0   70                               Barnyard 2 leaf                                                                           -- -- 70  -- Bedstraw    100                                                                               100                                                                               100 100                              Barnyardgrass                                                                             100                                                                               100                                                                               --  100                                                                               Blackgrass  -- 100                                                                               50  90                               Bedstraw   100                                                                               100                                                                               100 100                                                                               Chickweed   80 100                                                                               100 90                               Blackgrass 0  100                                                                               40  95 Corn        0  80 0   90                               Chickweed  90 100                                                                               --  100                                                                               Cotton      0  98 0   100                              Corn       10 60 40  80 Crabgrass   50 100                                                                               50  100                              Cotton     100                                                                               100                                                                               100 100                                                                               Downy Brome 0  90 10  90                               Crabgrass  0  70 30  70 Giant foxtail                                                                              80 100                                                                               60  100                              Downy Br=e 0  90 50  70 Lambsquarters                                                                              95 100                                                                               100 100                              Duck salad 0  70 0   70 Morningglory                                                                               0  100                                                                               10  100                              Giant foxtail                                                                             0  100                                                                               50  90 Pigweed     100                                                                               100                                                                               100 100                              Lambsquarters                                                                             90 100                                                                               --  100                                                                               Rape        20 100                                                                               30  100                              Morningglory                                                                              100                                                                               100                                                                               50  100                                                                               Ryegrass    0  100                                                                               60  95                               Pigweed    100                                                                               100                                                                               100 100                                                                               Sorghum     20 100                                                                               10  100                              Rape       100                                                                               100                                                                               80  100                                                                               Soybean     0  100                                                                               0   100                              Rice Japonica                                                                             65 100                                                                               70  95 Speedwell   100                                                                               100                                                                               100 --                               Ryegrass   0  100                                                                               40  90 Sugar beet  80 100                                                                               90  100                              Sorghum    0  98 50  90 Velvetleaf  95 100                                                                               100 100                              Soybean    70 100                                                                               60  90 Wheat       0  60 0   90                               Speedwell  100                                                                               100                                                                               100 -- Wild buckwheat                                                                             100                                                                               100                                                                               100 100                              Sugar beet 100                                                                               100                                                                               100 100                                                                               Wild oat    0  95 0   90                               Umbrella sedge                                                                            0  55 0   75                                                        Velvetleaf 100                                                                               100                                                                               100 100                                                       Wheat      0  60 30  90                                                        Wild buckwheat                                                                            100                                                                               100                                                                               100 100                                                       Wild oat   0  60 40  85                                                        __________________________________________________________________________                COMPOUND                 COMPOUND                                   Rate 8 g/ha  9   12      Rate 8 g/ha                                                                               12                                         __________________________________________________________________________     POSTEMERGENCE            PREEMERGENCE                                          Barley Igri  60  --      Barley Igri                                                                               0                                          Barnyard 2 leaf                                                                             --  --      Bedstraw   20                                         Barnyardgrass                                                                               100 20      Blackgrass 20                                         Bedstraw     100 --      Chickweed  0                                          Blackgrass   50  --      Corn       20                                         Chickweed    100 --      Cotton     0                                          Corn         60  --      Crabgrass  50                                         Cotton       100 --      Downy Brome                                                                               0                                          Crabgrass    60  --      Giant foxtail                                                                             60                                         Downy Brome  50  --      Lambsquarters                                                                             70                                         Duck salad   80  0       Morningglory                                                                              20                                         Giant foxtail                                                                               80  --      Pigweed    100                                        Lambsquarters                                                                               100 --      Rape       20                                         Morningglory 100 --      Ryegrass   20                                         Pigweed      100 --      Sorghum    20                                         Rape         90  --      Soybean    20                                         Rice Japonica                                                                               95  45      Speedwell  70                                         Ryegrass     50  --      Sugar beet 20                                         Sorghum      70  --      Velvetleaf 100                                        Soybean      100 --      Wheat      20                                         Speedwell    100 --      Wild buckwheat                                                                            30                                         Sugar beet   100 --      Wild oat   20                                         Umbrella sedge                                                                              90  0                                                             Velvetleaf   100 --                                                            Wheat        30  --                                                            Wild buckwheat                                                                              100 --                                                            Wild oat     30  --                                                            __________________________________________________________________________                COMPOUND                 COMPOUND                                   Rate 4 g/ha                                                                               3     4 11    Rate 4 g/ha  4   11                                   __________________________________________________________________________     POSTEMERGENCE            PREEMERGENCE                                          Barley Igri                                                                               --    20                                                                               40    Barley Igri  0   30                                   Barnyard 2 leaf                                                                           --    20                                                                               --    Bedstraw     20  100                                  Barnyardgrass                                                                             50    --                                                                               80    Blackgrass   10  30                                   Bedstraw   --    70                                                                               80    Chickweed    70  70                                   Blackgrass --    40                                                                               50    Corn         0   60                                   Chickweed  --    --                                                                               60    Cotton       0   80                                   Corn       --    30                                                                               50    Crabgrass    0   85                                   Cotton     --    60                                                                               100   Downy Brome  0   50                                   Crabgrass  --    20                                                                               50    Giant foxtail                                                                               20  90                                   Downy Brome                                                                               --    30                                                                               50    Lambsquarters                                                                               50  100                                  Duck salad 0     0 0     Morningglory 0   30                                   Giant foxtail                                                                             --    30                                                                               60    Pigweed      100 100                                  Lambsquarters                                                                             --    --                                                                               100   Rape         0   70                                   Morningglory                                                                              --    50                                                                               90    Ryegrass     0   60                                   Pigweed    --    30                                                                               60    Sorghum      0   60                                   Rape       --    50                                                                               80    Soybean      0   60                                   Rice Japonica                                                                             25    35                                                                               90    Speedwell    30  --                                   Ryegrass   --    30                                                                               75    Sugar beet   0   95                                   Sorghum    --    40                                                                               50    Velvetleaf   20  100                                  Soybean    --    40                                                                               80    Wheat        0   40                                   Speedwell  --    70                                                                               --    Wild buckwheat                                                                              0   100                                  Sugar beet --    90                                                                               85    Wild oat     0   50                                   Umbrella sedge                                                                            0     0 30                                                          Velvetleaf --    30                                                                               100                                                         Wheat      --    30                                                                               50                                                          Wild buckwheat                                                                            --    60                                                                               90                                                          Wild oat   --    20                                                                               60                                                          __________________________________________________________________________                COMPOUND                 COMPOUND                                   Rate 2 g/ha  9   12      Rate 2 g/ha                                                                               12                                         __________________________________________________________________________     POSTEMERGENCE            PREEMERGENCE                                          Barley Igri  30  --      Barley Igri                                                                               0                                          Barnyard 2 leaf                                                                             --  --      Bedstraw   0                                          Barnyardgrass                                                                               85  0       Blackgrass 0                                          Bedstraw     100 --      Chickweed  0                                          Blackgrass   40  --      Corn       0                                          Chickweed    100 --      Cotton     0                                          Corn         40  --      Crabgrass  20                                         Cotton       90  --      Downy Brome                                                                               0                                          Crabgrass    40  --      Giant foxtail                                                                             20                                         Downy Brome  30  --      Lambsquarters                                                                             0                                          Duck salad   30  0       Morningglory                                                                              20                                         Giant foxtail                                                                               50  --      Pigweed    20                                         Lambsquarters                                                                               100 --      Rape       0                                          Morningglory 70  --      Ryegrass   0                                          Pigweed      100 --      Sorghum    0                                          Rape         60  --      Soybean    0                                          Rice Japonica                                                                               80  20      Speedwell  0                                          Ryegrass     30  --      Sughr beet 0                                          Sorghum      50  --      Velvetleaf 20                                         Soybean      80  --      Wheat      0                                          Speedwell    100 --      Wild buckwheat                                                                            20                                         Sugar beet   85  --      Wild oat   0                                          Umbrella sedge                                                                              90  0                                                             Velvetleaf   100 --                                                            Wheat        25  --                                                            Wild buckwheat                                                                              100 --                                                            Wild oat     25  --                                                            __________________________________________________________________________                COMPOUND                 COMPOUND                                   Rate 1 g/ha                                                                               3     4 11    Rate 2 g/ha  4   11                                   __________________________________________________________________________     POSTEMERGENCE            PREEMERGENCE                                          Barley Igri                                                                               --    10                                                                               20    Barley Igri  0   0                                    Barnyard 2 leaf                                                                           --    10                                                                               --    Bedstraw     0   10                                   Barnyardgrass                                                                             20    --                                                                               0     Blackgrass   0   0                                    Bedstraw   --    30                                                                               70    Chickweed    0   70                                   Blackgrass --    20                                                                               30    Corn         0   0                                    Chickweed  --    --                                                                               30    Cotton       0   10                                   Corn       --    20                                                                               30    Crabgrass    0   10                                   Cotton     --    20                                                                               90    Downy Brome  0   0                                    Crabgrass  --    10                                                                               10    Giant foxtail                                                                               10  20                                   Downy Brome                                                                               --    10                                                                               20    Lambsquarters                                                                               0   100                                  Duck salad 0     0 0     Morningglory 0   10                                   Giant foxtail                                                                             --    20                                                                               20    Pigweed      60  50                                   Lambsquarters                                                                             --    --                                                                               100   Rape         0   0                                    Morningglory                                                                              --    40                                                                               85    Ryegrass     0   10                                   Pigweed    --    30                                                                               60    Sorghum      0   0                                    Rape       --    10                                                                               40    Soybean      0   0                                    Rice Japonica                                                                             0     20                                                                               45    Speedwell    0   --                                   Ryegrass   --    10                                                                               30    Sugar beet   0   20                                   Sorghum    --    20                                                                               20    Velvetleaf   --  100                                  Soybean    --    20                                                                               50    Wheat        0   0                                    Speedwell  --    10                                                                               --    Wild buckwheat                                                                              0   60                                   Sugar beet --    40                                                                               70    Wild oat     0   10                                   Umbrella sedge                                                                            0     0 20                                                          Velvetleaf --    20                                                                               60                                                          Wheat      --    10                                                                               20                                                          Wild buckwheat                                                                            --    20                                                                               50                                                          Wild oat   --    10                                                                               20                                                          __________________________________________________________________________

TEST C

Compounds evaluated-in this test were formulated in a non-phytoxic solvent and applied to the soil surface before plant seedlings emerged (preemergence application) and to plants that were in the one-to-four leaf stage (postemergence application). A sandy loam soil was used for the preemergence test while a mixture of sandy loam soil and greenhouse potting mix in a 60:40 ratio was used for the postemergence test. Test compounds were applied within approximately one day after planting seeds for the preemergence test.

Plantings of these crops and weed species were adjusted to produce plants of appropriate size for the postemergence test. All plant species were grown using normal greenhouse practices. Crop and weed species include winter barley (Hordeurn vulgate cv. `Igri`), blackgrass (Alopecurus myosuroides), chickweed (Steliaria media), downy brome (Bromus tectorum), field violet (Viola arvensis), galium (Galium aparine), green foxtail (Setaria viridis), kochia (Kochia scoparia), lambsquarters (Chenopodium album), speedwell (Veronica persica), rape (Brassica napus), ryegrass (Lolium multiflorum), sugar beet (Beta vulgaris cv. `US1`), sunflower (Helianthus annuus cv. `Russian Giant`), spring wheat (Triticum aestivum cv. `ERA`), winter wheat (Triticum aestivum cv. `Talent`), wild buckwheat (Polygonurn convolvulus), wild mustard (Sinapis arvensis), wild oat (Avena fatua), and wild radish (Raphanus raphanistrum).

Blackgrass, galium and wild oat were treated at two growth stages. The first stage (1) was when the plants had two to three leaves. The second stage (2) was when the plants had approximately four leaves or in the initial stages of tillering. Treated plants and untreated controls were maintained in a greenhouse for approximately 21 to 28 days, after which all treated plants were compared to untreated controls and visually evaluated. Plant response ratings, summarized in Table C, are based upon a 0 to 100 scale where 0 is no effect and 100 is complete control. A dash response (--) indicates no test result.

                                      TABLE C                                      __________________________________________________________________________                   COMPOUND                                                                               COMPOUND  COMPOUND  COMPOUND                                                                               COMPOUND                     PREEMERGENCE  12      1     12  1     12  1   12  1                            __________________________________________________________________________                   Rate 125                            Rate 8                                     g/ha    Rate 64 g/ha                                                                             Rate 32 g/ha                                                                             Rate 16 g/ha                                                                           g/ha                         Blackgrass (1)                                                                               30      20    10  0     0   0   0   0                            Blackgrass (2)                                                                               30      20    20  0     0   0   0   0                            Chickweed     0       100   0   85    0   55  0   25                           Downy brome   40      20    20  0     20  0   10  0                            Field violet  100     80    100 60    80  30  40  0                            Galium (1)    100     100   100 75    80  50  30  30                           Galium (2)    100     100   100 70    100 45  40  25                           Green foxtail 100     100   100 100   --  80  70  35                           Kochia        100     100   90  90    90  60  0   35                           Lambsquarters 100     --    100 --    100 --  80  --                           Persn Speedwell                                                                              100     100   100 90    100 45  100 20                           Rape          80      65    60  35    0   0   0   0                            Ryegrass      90      85    60  70    10  40  0   20                           Sugar beet    100     100   100 95    100 65  100 45                           Sunflower     25      25    20  0     0   0   0   0                            Wheat (Spring)                                                                               50      0     40  0     20  0   10  0                            Wheat (Winter)                                                                               60      0     45  0     25  0   10  0                            Wild buckwheat                                                                               100     100   100 85    100 60  70  30                           Wild mustard  100     100   100 70    100 50  70  20                           Wild oat (1)  80      25    50  0     20  0   0   0                            Wild oat (2)  90      30    55  0     40  0   30  0                            Wild radish   100     60    80  45    50  20  0   0                            Winter Barley 50      0     30  0     25  0   10  0                            __________________________________________________________________________                COMPOUND                                                                               COMPOUND COMPOUND  COMPOUND                                                                               COMPOUND                                                                               COMPOUND                 POSTEMERGENCE                                                                             1       1    9   1    9   1    9   9       9                        __________________________________________________________________________                Rate 64                            Rate 4  Rate 2                              g/ha    Rate 32 g/ha                                                                            Rate 16 g/ha                                                                            Rate 8 g/ha                                                                             g/ha    g/ha                     Blackgrass (1)                                                                            0       0    40  0    35  0    35  30      20                       Blackgrass (2)                                                                            0       0    50  0    20  0    0   0       0                        Chickweed  55      25   100 0    100 0    100 100     100                      Downy brome                                                                               0       0    40  0    40  0    40  10      10                       Field violet                                                                              100     100  100 75   100 35   100 100     50                       Galium (1) 95      60   100 30   100 0    100 100     100                      Galium (2) 100     65   100 30   100 0    100 100     40                       Green foxtail                                                                             35      0    100 0    100 0    75  75      40                       Kochia     90      60   100 20   100 0    100 100     70                       Lambsquarters                                                                             --      --   100 --   100 --   100 100     70                       Persn Speedwell                                                                           70      55   100 30   100 0    100 100     40                       Rape       90      50   160 25   80  0    50  50      0                        Ryegrass   60      30   100 0    70  0    30  0       0                        Sugar beet 100     100  100 90   100 60   100 100     80                       Sunflower  55      30   60  0    --  0    60  50      --                       Wheat (Spring)                                                                            0       0    55  0    50  0    30  20      20                       Wheat (Winter)                                                                            0       0    40  0    30  0    20  20      20                       Wild buckwheat                                                                            100     95   100 65   100 25   100 50      --                       Wild mustard                                                                              100     90   100 55   100 20   60  60      40                       Wild oat (1)                                                                              0       0    60  0    60  0    20  10      10                       Wild oat (2)                                                                              0       0    80  0    60  0    40  20      10                       Wild radish                                                                               85      50   --  25   100 0    50  50      30                       Winter Barley                                                                             0       0    40  0    40  0    20  15      15                       __________________________________________________________________________

TEST D

Seeds, rhizomes, or plant parts of alfalfa (Medicago sativa), bermudagrass (Cynodon dactylon), broadleaf signalgrass (Brachiaria plantyphylla), common ragweed (Ambrosia elatior), dallisgrass (Paspalum Dilatatum), goosegrass (Eleusine indica), guineagrass (Panicurn maximum), itchgrass (Rottboellia exaltata), johnsongrass (Sorghum halepense), ann bluegrass (Poa annua), large crabgrass (Digitaria sanguinalis), P. J. legume (Pueraria javanica), pitted morningglory (Ipomoea lacunosa), peanuts (Arachis hypogaea), purple nutsedge (Cyperus rotundus), sandbur (Cenchrus echinatus), smooth crabgrass (Digitaria ischaemum), common purslane (Portulaca oleracea), TX panicurn (Panicurn texanurn) and yellow nutsedge (Cyperus esculentus) were planted into greenhouse pots containing greenhouse planting medium.

Each pot contained only one plant species. The test compound was dissolved in a non-phytotoxic solvent and applied preemergence and/or postemergence to the plants.

Preemergence applications were made within one day of planting the seeds or plant parts. Postemergence applications were applied when the plants were in the two to four leaf stage (three to twenty cm).

Test chemicals were dissolved in a non-phytotoxic solvent and applied preemergence and postemergence to the plants. Untreated control plants and treated plants were placed in the greenhouse and visually evaluated for injury at 13 to 21 days after herbicide application.

Plant response ratings, summarized in Table D, are based on a 0 to 100 scale where 0 is no injury and 100 is complete control. A dash (--) response indicates no test result.

                                      TABLE D                                      __________________________________________________________________________                COM- COM-                                                                      POUND                                                                               POUND COMPOUND                                                 POSTEMERGENCE                                                                             8     3   8  16                                                                           1  3  4  5 6 8  9  11 12 13 14                                                                               15 16                                                                               17 18                 __________________________________________________________________________                Rate                                                                           1000 Rate 500                                                                  g/ha g/ha  Rate 250 g/ha                                            Alfalfa Var.                                                                              30   100  40  0                                                                           50 100                                                                               60 0 10                                                                               40 100                                                                               100                                                                               0  40 30                                                                               10 10                                                                               0  0                  Ann Bluegrass                                                                             30   100  40  0                                                                           100                                                                               100                                                                               50 0 0 20 -- 20 0  -- --                                                                               -- 0 0  0                  Bermudagrass                                                                              60   100  80  0                                                                           0  100                                                                               60 0 0 40 100                                                                               100                                                                               0  70 0 0  0 0  0                  Brdlf Sgnlgrass                                                                           70   100 100  0                                                                           0  100                                                                               70 0 0 20 100                                                                               100                                                                               0  10 0 0  0 0  0                  Cmn Purslane                                                                              90   100 100 30                                                                           100                                                                               100                                                                               100                                                                               0 0 100                                                                               100                                                                               100                                                                               90 100                                                                               80                                                                               70 20                                                                               20 20                 Cmn Ragweed                                                                               --   --  --   0                                                                           90 100                                                                               -- --                                                                               --                                                                               -- -- -- -- -- --                                                                               -- 0 100                                                                               100                Dallisgrass                                                                               60   100  90  0                                                                           50 100                                                                               90 0 0 0  100                                                                               100                                                                               0  70 0 0  0 0  0                  Goosegrass 60   100  90  0                                                                           20 100                                                                               70 0 0 0  100                                                                               100                                                                               0  90 0 0  0 0  0                  Guineagrass                                                                               20   100  50  0                                                                           0  100                                                                               50 0 0 10 100                                                                               100                                                                               0  0  0 0  0 0  0                  Itchgrass  30   100  50  0                                                                           0  100                                                                               50 0 0 0  100                                                                               100                                                                               0  40 0 0  0 0  0                  Johnsongrass                                                                              50   100  70  0                                                                           20 100                                                                               100                                                                               0 0 80 100                                                                               100                                                                               0  90 0 0  0 0  0                  Large Crabgrass                                                                           50   100  30  0                                                                           0  100                                                                               60 0 0 20 100                                                                               100                                                                               0  100                                                                               0 0  0 0  0                  P J Legume --   --  --  --                                                                           20 100                                                                               -- --                                                                               --                                                                               -- -- -- -- -- --                                                                               -- --                                                                               -- --                 Peanuts    70    90  60 20                                                                           20 100                                                                               50 0 10                                                                               20 80 90 20 50 0 20 0 30 60                 Pit Morninglory                                                                           60   100  70  0                                                                           0  100                                                                               90 0 0 30 100                                                                               100                                                                               0  50 0 0  0 0  30                 Purple Nutsedge                                                                           --   --   0 --                                                                            0  90 0  0 0 0  70 90 -- 0  0 10 --                                                                               0  0                  S. Sandbur 60   100  20  0                                                                           0  100                                                                               60 0 0 0  100                                                                               100                                                                               0  0  0 0  0 0  0                  Smooth Crabgras                                                                           40   100  50  0                                                                           0  100                                                                               60 0 0 20 90 100                                                                               0  80 0 0  0 0  0                  Texas Panicum                                                                             40   100  20 --                                                                           0  100                                                                               90 0 0 0  -- -- -- -- --                                                                               -- --                                                                               -- --                 Yellow Nutsedge                                                                           --   --   0 --                                                                            0  100                                                                               0  0 0 0  100                                                                               100                                                                               -- 0  0 20 --                                                                               0  0                  __________________________________________________________________________                COMPOUND                       COMPOUND    COMPOUND                 POSTEMERGENCE                                                                             1  2  3  8  9  11 12 13 14                                                                               15                                                                               16 3   11  12  3   11                   __________________________________________________________________________                Rate 125 g/ha                  Rate 64 g/ha                                                                               Rate 32 g/ha             Alfalfa Var.                                                                              50 70 100                                                                               0  100                                                                               100                                                                               0  0  0 0 10 90  60  0   80  30                   Ann Bluegrass                                                                             -- -- 100                                                                               0  -- 0  0  -- --                                                                               --                                                                               0  60  0   0   50  0                    Bermudagrass                                                                              0  -- 100                                                                               0  80 100                                                                               0  0  0 0 70 0   0   70  0                        Brdlf Sgnlgrass                                                                           0  0  100                                                                               0  100                                                                               100                                                                               0  0  0 0 0  100 30  0   90  0                    Cmn Purslane                                                                              100                                                                               100                                                                               100                                                                               60 100                                                                               100                                                                               0  100                                                                               70                                                                               60                                                                               20 100 100 40  100 100                  Cmn Ragweed                                                                               50 90 100                                                                               -- -- -- -- -- --                                                                               --                                                                               0  --  --  --  --  --                   Dallisgrass                                                                               0  100                                                                               100                                                                               0  100                                                                               100                                                                               0  0  0 0 0  100 0   0   90  0                    Goosegrass 0  80 100                                                                               0  100                                                                               100                                                                               0  0  0 0 0  100 30  0   80  0                    Guineagrass                                                                               0  0  100                                                                               0  80 100                                                                               0  0  0 0 0  100 0   0   40  0                    Itchgrass  0  0  100                                                                               0  60 90 0  0  0 0 0  70  70  0   50  0                    Johnsongrass                                                                              20 0  100                                                                               0  100                                                                               100                                                                               0  0  0 0 0  100 40  0   100 20                   Large Crabgrass                                                                           0  0  100                                                                               0  90 100                                                                               0  0  0 0 0  100 0   0   20  0                    P J Legume 20 80 90 -- -- -- -- -- --                                                                               --                                                                               -- --  --  --  --  --                   Peanuts    10 0  100                                                                               20 80 80 0  0  0 0 0  100 30  0   70  50                   Pit Morninglory                                                                           0  40 100                                                                               30 100                                                                               100                                                                               0  0  0 0 0  100 30  0   100 50                   Purple Nutsedge                                                                           0  0  90 0  60 80 -- 0  0 0 -- 80  --  --  20  --                   S. Sandbur 0  0  100                                                                               0  100                                                                               100                                                                               0  0  0 0 0  90  0   0   20  0                    Smooth Crabgras                                                                           0  -- 100                                                                               0  80 80 0  0  0 0 0  80  0   0   40  0                    Texas Panicum                                                                             0  0  100                                                                               -- -- -- -- -- --                                                                               --                                                                               -- 100 --  --  80  --                   Yellow Nutsedge                                                                           0  0  100                                                                               0  100                                                                               100                                                                               -- 0  0 0 -- 100 --  --  20  --                   __________________________________________________________________________                COMPOUND                                                                               COMPOUND                                                    PREEMERGENCE                                                                              8   16  1  3  4  5 6  8  9  11 12 13 14 15 16 17 18                 __________________________________________________________________________                Rate 500 g/ha                                                                          Rate 250 g/ha                                               Alfalfa Var.                                                                              80  0   80 100                                                                               100                                                                               0 0  50 100                                                                               100                                                                               100                                                                               0  0  0  0  20 60                 Ann Bluegrass                                                                             100 0   20 100                                                                               100                                                                               0 0  70 100                                                                               100                                                                               60 70 0  0  0  0  100                Bermudagrass                                                                              100 90  20 100                                                                               100                                                                               0 0  100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90 30 40 30 100                Brdlf Sgnlgrass                                                                           100 0   0  100                                                                               100                                                                               0 0  70 100                                                                               100                                                                               90 0  0  0  0  0  100                Cmn Purslane                                                                              100 0   100                                                                               100                                                                               100                                                                               0 0  100                                                                               100                                                                               100                                                                               100                                                                               60 0  0  0  0  0                  Cmn Ragweed                                                                               --  20  100                                                                               100                                                                               -- --                                                                               -- -- -- -- -- -- -- -- 0  0  80                 Dallisgrass                                                                               100 90  100                                                                               100                                                                               100                                                                               0 0  100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               80 20 100                Goosegrass 100 80  100                                                                               100                                                                               100                                                                               0 0  100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               0  90 100                Guineagrass                                                                               100 100 70 100                                                                               100                                                                               0 0  100                                                                               100                                                                               100                                                                               100                                                                               70 0  0  0  60 100                Itchgrass  80  0   0  100                                                                               100                                                                               0 0  60 100                                                                               100                                                                               80 20 0  0  0  0  70                 Johnsongrass                                                                              100 0   30 100                                                                               100                                                                               0 0  90 100                                                                               100                                                                               100                                                                               0  0  0  0  0  70                 Large Crabgrass                                                                           100 90  100                                                                               100                                                                               100                                                                               0 0  100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90 80 30 70 100                Peanuts    70  0   0  100                                                                               40 0 0  10 30 100                                                                               0  10 0  0  0  20 50                 Pit Morninglory                                                                           90  0   50 100                                                                               80 0 0  70 100                                                                               100                                                                               60 0  0  0  0  20 60                 Purple Nutsedge                                                                           80  --  0  100                                                                               10 0 0  80 50 90 -- 0  0  0  -- 0  0                  S. Sandbur 100 0   0  100                                                                               100                                                                               0 0  70 100                                                                               100                                                                               100                                                                               90 0  0  0  0  100                Smooth Crabgras                                                                           100 100 100                                                                               70 100                                                                               0 0  100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               30 100                                                                               80 70 100                Texas Panicum                                                                             90  --  90 100                                                                               100                                                                               0 0  90 -- -- -- -- -- -- -- -- --                 Yellow Nutsedge                                                                           80  --  0  90 20 0 0  70 80 90 -- 20 0  0  -- 0  60                 __________________________________________________________________________                COMPOUND                       COMPOUND   COMPOUND                  PREEMERGENCE                                                                              1  2  3  8  9  11 12 13 14                                                                               15                                                                               16 3  11  12  3    11                   __________________________________________________________________________                Rate 125 g/ha                  Rate 64 g/ha                                                                              Rate 32 g/ha              Alfalfa Var.                                                                              0  50 100                                                                               0  100                                                                               100                                                                               80 0  0 0 0  100                                                                               100 20  70   100                  Ann Bluegrass                                                                             0  0  100                                                                               10 100                                                                               100                                                                               0  60 0 0 0  100                                                                               60  0   90   30                   Bermudagrass                                                                              0  30 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               0  70                                                                               30                                                                               0  100                                                                               100 90  100  100                  Brdlf Sgnlgrass                                                                           0  0  100                                                                               10 100                                                                               100                                                                               0  0  0 0 0  100                                                                               100 0   90   30                   Cmn Purslane                                                                              50 100                                                                               100                                                                               90 100                                                                               100                                                                               30 20 0 0 0  100                                                                               100 80  100  100                  Cmn Ragweed                                                                               100                                                                               100                                                                               100                                                                               -- -- -- -- -- --                                                                               --                                                                               0  -- --  --  --   --                   Dallisgrass                                                                               10 30 100                                                                               100                                                                               100                                                                               100                                                                               70 100                                                                               20                                                                               20                                                                               0  100                                                                               100 100 100  100                  Goosegrass 10 90 100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90                                                                               90                                                                               0  100                                                                               100 100 100  100                  Guineagrass                                                                               0  0  100                                                                               100                                                                               100                                                                               100                                                                               30 100                                                                               0 0 100                                                                               100                                                                               90  100 90                        Itchgrass  0  0  100                                                                               50 100                                                                               100                                                                               0  0  0 0 0  100                                                                               100 0   100  60                   Johnsongrass                                                                              0  0  100                                                                               50 100                                                                               100                                                                               0  30 0 0 0  100                                                                               100 50  90   70                   Large Crabgrass                                                                           90 0  100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               100                                                                               90                                                                               80                                                                               0  100                                                                               100 100 100  100                  Peanuts    0  0  80 0  80 70 0  0  0 0 0  40 60  0   50   0                    Pit Morninglory                                                                           0  0  100                                                                               0  100                                                                               100                                                                               50 0  0 0 0  100                                                                               100 0   100  20                   Purple Nutsedge                                                                           0  70 90 10 10 80 -- 0  0 0 -- 80 --  --  60   --                   S. Sandbur 0  90 100                                                                               0  100                                                                               100                                                                               0  0  0 0 0  100                                                                               100 0   100  80                   Smooth Crabgras                                                                           20 0  100                                                                               100                                                                               100                                                                               100                                                                               90 100                                                                               0 0 0  100                                                                               100 70  100  100                  Texas Panicum                                                                             20 0  100                                                                               0  -- -- -- -- --                                                                               --                                                                               -- 100                                                                               --  --  90   --                   Yellow Nutsedge                                                                           0  0  80 0  30 90 -- 0  0 0 -- 80 --  --  70   --                   __________________________________________________________________________

TEST E

Plastic windowsill flats were filled with planting medium and sprayed with the test compounds formulated in a non-phytotoxic spray solution. Treated soil was then placed in plastic bags and shaken thoroughly to incorporate the compounds in the soil. Seedings of cabbage (Early Copenhagen variety) and tomato (Rutgers Select and Ramapo VF FL hybrid varieties) were transplanted into the spiked soil. Untreated or antidote (naphthalic anyhdride) treated corn seeds were also planted into the spiked soil.

Plants were visually rated and compared with the appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table E.

                                      TABLE E                                      __________________________________________________________________________             Rate     Tomato                                                                               Tomato                                                                              Corn  Corn                                         COMPOUND                                                                               g/ha                                                                              Cabbage                                                                              Rutgers                                                                              Ramapo                                                                              Untreated                                                                            Treated                                      __________________________________________________________________________                (14 DAT)         (10 DAT)                                           3       4  10    15    15   0     0                                                    8  45    85    75   0     0                                                    16 70    100   100  40    0                                                    32 100   100   100  70    10                                                   64 100   100   100  80    30                                                            (32 DAT)   (28 DAT)                                           3       4  0     0     0    0     0                                                    8  10    100   45   0     0                                                    16 60    100   100  25    0                                                    32 100   100   100  65    40                                                   64 100   100   100  90    70                                                            (14 DAT)   (10 DAT)                                           8       32 0     0     0    0     0                                                    64 0     0     0    0     0                                                    125                                                                               10    0     0    0     0                                                    250                                                                               65    15    5    0     0                                                    500                                                                               60    55    55   0     0                                                             (32 DAT)   (28 DAT)                                           8       32 0     0     0    0     0                                                    64 0     0     0    0     0                                                    125                                                                               0     0     0    0     0                                                    250                                                                               50    0     0    10    0                                                    500                                                                               55    30    20   10    0                                            __________________________________________________________________________

TEST F

Sugarcane varieties CP70-321 and CP70-330 were planted in 15.2 cm plastic pots which were also seeded with large crabgrass (Digitaria sanguinalis) and Lalang (Imperata cylindrica) rhizomes were planted in 20.3 cm plastic pots which also had volunteer fern (Nephrolepis pectinata) plants growing in them. In another test, guineagrass (Panicum maximum, Paspalura conjugatum, Asystasia intrusa and Nephrolepis pectinata plants were grown in planting medium in plastic pots. The plants were treated pcstemergence with the test compounds formulated in a non-phytotoxic spray solution.

Treated plants were visually rated at the end of the test and compared with the appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shownin Table F.

                                      TABLE F                                      __________________________________________________________________________             Rate                                                                              Sugarcane   Large                                                   COMPOUND                                                                               g/ha                                                                              CP70-321                                                                             CP70-330                                                                             Crabgrass                                                                             Lalang                                                                             Fern                                         __________________________________________________________________________     3       32 0     0     50     30  0                                                    64 0     0     60     30  0                                                    125                                                                               0     0     85     30  0                                            8       500                                                                               0     0     0      0   0                                                    1000                                                                              0     0     30     30  0                                                    2000                                                                              0     0     60     60  20                                           __________________________________________________________________________             Rate      Paspalum                                                                              Asystasia                                                                           Nephrolepis                                      COMPOUND                                                                               g/ha                                                                              Guineagrass                                                                           Conjugalum                                                                            intrusa                                                                             pectinate                                        __________________________________________________________________________     11      64 40     0      45   0                                                        125                                                                               50     0      40   0                                                        250                                                                               75     30     50   0                                                        500                                                                               80     45     60   0                                                12      64 0      0      0    0                                                        125                                                                               0      0      0    0                                                        250                                                                               30     0      0    0                                                        500                                                                               30     0      0    0                                                __________________________________________________________________________

TEST G

Sugarcane (Saccharum officinarum), purple nutsedge (Cyperus rotundus), Brachiaria decumbens and Brachiaria plantaginea were planted in fiberglass trays. Plants were treated postemergence with the test compounds formulated in a non-phytotoxic spray solution.

Treated plants were visually rated and compared with appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table G.

                  TABLE G                                                          ______________________________________                                         COM-   Rate             Purple Brachiaria                                                                             Brachiaria                              POUND  g/ha   Sugarcane nutsedge                                                                              decumbens                                                                              plantaginea                             ______________________________________                                         8      500    0         20     90      60                                             1000   0         30     100     80                                             2000   20        60     100     100                                     11     32     0         0      0       0                                              64     10        0      70      60                                             125    30        0      90      90                                      12     64     0         0      0       0                                              125    0         0      0       0                                       ______________________________________                                    

TEST H

Pineapple (Ananas comosus), guineagrass (Panicurn maximum) and swollen fingergrass (Chloris inflata) were planted in potting medium. Plants were treated postemergence with the test compound formulated in a non-phytotoxic spray solution.

Treatments were visually rated and compared with the appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table H.

                  TABLE H                                                          ______________________________________                                                   Rate                      Swollen                                    COMPOUND  g/ha   Pineapple Guineagrass                                                                             fingergrass                                ______________________________________                                         8         250    0         0        0                                                    500    0         0                                                             1000   0         30                                                            2000   0         40       80                                         ______________________________________                                    

TEST I

Cuttings of turf species Zoysia spp., and St. Augustine (Stenotaphrum secundatum) were planted in 11.4 cm plastic pots filled with planting medium. Smooth crabgrass (Digitaria ischaemum) and large crabgrass (Digitaria sanguinalis) seeds were also planted and grown in 11.4 cm plastic pots. Plants were treated postemergence with the test compounds.

Treatments were visually rated at the end of the test and compared with the appropriate controls. Injury ratings were based on a scale of 0 to 100 where indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table I.

                  TABLE I                                                          ______________________________________                                         COM-   Rate                    Smooth  Large                                   POUND  g/ha   Zoysia  St. Augustine                                                                           Crabgrass                                                                              Crabgrass                               ______________________________________                                         3      4      0       0        0       0                                              8      0       0        0       0                                              16     0       0        10      40                                             32     0       0        10      50                                             64     0       0        30      70                                      8      64     0       0        0       0                                              125    30      0        0       50                                             250    50      20       20      90                                             500    50      20       40      90                                      ______________________________________                                    

TEST J

Fifteen different soybean varieties including Williams, W-20 and the Asgrow varieties A3242, A3935, A4715, A5979, A3322, A4009, A4906, A6297, A3205, A3733, A4595, A5403 and A6961 were planted separately in plastic pots filled with planting medium. The pots were tested preemergence with the test chemicals formulated in a non-phytotoxic spray solution.

Plants were visually rated at the end of the test and compared with the appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table J.

                                      TABLE J                                      __________________________________________________________________________             Rate                                                                   COMPOUND                                                                               g/ha Williams                                                                            W20 A3205                                                                              A3242                                                                              A3322                                                                              A3733                                                                              A3935                                                                              A4009                                __________________________________________________________________________     11      16   20   20  20  20  20  30  20  40                                           32   60   50  50  60  50  50  70  70                                           64   90   90  80  90  90  90  90  90                                           125  100  100 100 100 100 100 100 100                                  12      16   0    0   0   0   0   0   0   0                                            32   0    0   0   0   0   0   0   0                                            64   0    0   0   0   0   0   0   0                                            125  20   20  20  20  20  20  20  20                                   __________________________________________________________________________             Rate                                                                   COMPOUND                                                                               g/ha A4595                                                                               A4715                                                                              A4906                                                                              A5403                                                                               A5979                                                                               A6297                                                                               A6961                                 __________________________________________________________________________     11      16   20   30  60  50   40   60   20                                            32   60   70  60  60   70   100  100                                           64   90   90  90  90   90   90   90                                            125  100  100 100 100  100  100  100                                   11      16   0    0   0   0    0    0    0                                             32   0    0   0   0    0    0    0                                             64   0    0   0   0    0    0    0                                             125  20   20  20  20   20   20   20                                    __________________________________________________________________________

TEST K

Corn, soybean, tomato, morningglory, different nightshade varieties [Solanum nigrum (entire and serrated leaf), S. nigrum subsp. nigrum, S. interius, S. ptycanthus (green berries and black berries), S. nigrum subsp. schultesii and triazine-tolerant nightshade] seeds and potato eye cuttings were planted in separate 11.4 cm plastic pots filled with planting medium. The pots were sprayed preemergence with the test chemicals formulated in a non-phytotoxic spray solvent.

Plants were visually rated at the end of the test and compared with appropriate controls. Injury ratings were based on a scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. Results are shown in Table K.

                                      TABLE K                                      __________________________________________________________________________                                    Triazine                                                Rate                   Tolerant                                        COMPOUND                                                                               g/ha                                                                              Corn                                                                              Soybean                                                                             Tomato                                                                              Morningglory                                                                          Nightshade                                                                            Potato                                   __________________________________________________________________________     11      2  0  0    0    0      0      0                                                4  30 20   20   40     0      20                                       12      16 0  0    0    0      0      0                                                32 0  0    0    20     --     0                                                64 0  0    20   40     70     20                                               125                                                                               0  0    60   50     100    60                                       __________________________________________________________________________                S. Nigrum                                                                            S. Nigrum                                                                            S. Nigrum   S. Ptyanthus                                        Rate                                                                              Entire                                                                               Serrated                                                                             Subs.       Green                                       COMPOUND                                                                               g/ha                                                                              Leaf  Leaf  Nigrum                                                                               S. Interius                                                                          Berries                                     __________________________________________________________________________     11      2  0     0     0     0     0                                                   4  0     0     0     0     0                                           12      16 0     0     0     0     0                                                   32 0     30    20    70    40                                                  64 0     70    60    100   100                                                 125                                                                               60    100   80    100   100                                         __________________________________________________________________________                          S. Ptyanthus                                                                          S. Nigrum                                                  Rate         Black  Sub.                                               COMPOUND                                                                               g/ha         Berries                                                                               Schultesii                                         __________________________________________________________________________     11      2            0      0                                                          4            0      0                                                  12      16           0      0                                                          32           0      0                                                          64           50     20                                                         125          70     60                                                 __________________________________________________________________________

TEST L

Rooted cuttings of rough lemon (Citrus sp.) were planted in 30 liter plastic pots. These pots were also seeded with guineagrass (Panicum maximum), sandbur (Cenchrus enchinatus) and pigweed (Amaranthus viridis). The weeds were cutback many times to simulate mowing and the citrus plant also trimmed.

The citrus was sprayed to simulate field type post-directed herbicide application while the weeds were treated postemergence over the top with the test compounds formulated in a non-phytotoxic spray solvent. In a separate test, loblolly pine seedlings were also sprayed over-the-top with the test compounds formulated in a non-phytotoxic spray solvent. Treated plants were visually rated and compared with appropriate controls. The injury ratings are based on the scale of 0 to 100 where 0 indicates no effect, 20 indicates minimal effect and 100 indicates complete control. The results are shown in Tables L1 and L2. The differences in results may be due to the fact that the tests were conducted using plants at different stages of growth.

                                      TABLE L1                                     __________________________________________________________________________               COM-  COM-  COM-            COM-  COM-  COM-                                   POUND POUND POUND           POUND POUND POUND                        POST-DIRECTED                                                                            1 2 3 1 2 3 1 2 3 OVER-THE-TOP                                                                             1 2 3 1 2 3 1 2 3                        __________________________________________________________________________               Rate (500                                                                            Rate (250                                                                            (125            Rate (50                                                                             Rate (250                                                                            Rate (125                              g/ha) g/ha) g/ha)           g/ha) g/ha) g/ha)                        Rough Lemon                                                                              0 0 0 0 0 0 0 0 0 Guineagrass                                                                              0 0 70                                                                               0 0 30                                                                               0 0 30                                                   Pigweed   0 0 70                                                                               0 0 40                                                                               0 0  0                                                   Sandbur   0 0 0 0 0 0 0 0  0                       __________________________________________________________________________

                                      TABLE L2                                     __________________________________________________________________________               COMPOUND COMPOUND          COMPOUND                                                                               COMPOUND                          POST-DIRECTED                                                                            3  5 6 8 8       OVER-THE-TOP                                                                             3 5 6 8 8                                 __________________________________________________________________________               Rate (250 g/ha)                                                                         Rate (125 g/ha)   Rate (250 g/ha)                                                                        Rate (125 g/ha)                   Rough Lemon                                                                              30*                                                                               0 0 0 0       Loblolly pine                                                                            70                                                                               0 0 0 0                                                            Guineagrass                                                                              70                                                                               0 0 20                                                                               10                                                           Pigweed   20                                                                               0 0 40                                                                               30                                                           Sandbur   60                                                                               0 0 30                                                                               10                                __________________________________________________________________________      *Compound contacted leaves after treatment.                               

What is claimed is:
 1. A method for controlling the growth of undesired vegetation in plantation crops which comprises applying to the locus of the crop an herbicidally effective amount of a compound of Formula I ##STR24## wherein ##STR25## A is O or S; R¹ is C₁ -C₄ alkyl optionally substituted with one or more halogen, OR⁵, SR⁶ or CN; C₃ -C₆ alkenyl or C₃ -C₆ alkynyl, each optionally substituted with 1-3 halogen atoms; formyl; or C₂ -C₆ alkanoyl;R² is H, allyl, propargyl, CH(CH₃)C.tbd.CH, benzyl, CHR⁷ CO₂ R⁸ or may be taken together with Z; R³ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or N(CH₃)₂ ; R⁵ and R⁶ are independently H or C₁ -C₃ alkyl; R⁷ and R⁸ are independently C₁ -C₂ alkyl; X is Cl or Br; Y is F or Cl; Z is H or may be taken together with R² as --CH₂ CHR⁹ such that the linking A atom is attached to the methine carbon; R⁹ is C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, cyclopropyl, vinyl, C₂ alkynyl, CN, C(O)R¹⁰, CO₂ R¹⁰, CONR¹⁰ R¹¹, CR¹² R¹³ C(O)R¹⁰, CR¹² R¹³ CO₂ R¹⁰, CR¹² R¹³ CONR¹⁰ R¹¹, CHR¹² OH, CHR¹² C(O)R¹⁰ or CHR¹² OC(O)NR¹⁰ R¹¹ ; and R¹⁰, R¹¹, R¹² and R¹³ are independently H or C₁ -C₃ alkyl.
 2. The method of claim 1,wherein R¹ is C₁ -C₃ alkyl optionally substituted with 1 to 3 F atoms or Cl atoms, O(C₁ -C₂ alkyl), S(C₁ -C₂ alkyl) or CN; C₃ -C₄ alkenyl optionally substituted with 1 to 3 F atoms or Cl atoms; C₃ -C₄ alkynyl; or C₂ -C₃ alkanoyl; R² is H, allyl, propargyl, CH(CH₃)C.tbd.CH, CHR⁷ CO₂ R⁸ or may be taken together with Z; R³ is C₁ -C₂ alkyl, C₁ -C₂ haloalkyl or N(CH₃)₂ ; and X is Cl.
 3. The method of claim 2, whereinR¹ is CH₃ optionally substituted with 1 to 3 F atoms or Cl atoms; CH₂ CN; allyl; or propargyl; and R³ is CF₃.
 4. The method of claim 2, wherein the compound of Formula I is3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]-phenyl]-6-dimethylamino-1-methyl-1,3,5-triazine-2,4(1H, 3H)-dione.
 5. The method of claim 2, wherein the compound of Formula I is 3-(7-chloro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione.
 6. The method of claim 1, wherein the compound of Formula I is applied in combination with at least one of the following: surfactant, solid or liquid diluent.
 7. The method of claim 1 wherein the plantation crop is citrus.
 8. A compound of Formula III ##STR26## wherein A is O or S;R¹ is C₁ -C₄ alkyl optionally substituted with one or more halogen, OR⁵, SR⁶ or CN; C₃ -C₆ alkenyl or C₃ -C₆ alkynyl, each optionally substituted with 1-3 halogen atoms; formyl; or C₂ -C₆ alkanoyl; R² is H, allyl, propargyl, CH(CH₃)C.tbd.CH, benzyl, CHR⁷ CO₂ R⁸ or may be taken together with Z; R³ is C₁ -C₄ alkyl, C₁ -C₄ haloalkyl or N(CH₃)₂ ; R⁵ and R⁶ are independently H or C₁ -₃ alkyl; R⁷ and R⁸ are independently C₁ -C₂ alkyl; X is Cl or Br; Y is F or Cl; Z is H or may be taken together with R² as --CH₂ CHR⁹ such that the linking A atom is attached to the methine carbon; R⁹ is C₁ -C₃ alkyl, C₁ -C₃ haloalkyl, cyclopropyl, vinyl, C₂ alkynyl, CN, C(O)R¹⁰, CO₂ R¹⁰, CONR¹⁰ R¹¹, CR¹² R¹³ C(O)R¹⁰, CR¹² R¹³ CO₂ R¹⁰, CR¹² R¹³ CONR¹⁰ R¹¹, CHR¹² OH, CHR¹² OC(O)R¹⁰ or CHR¹² OC(O)NR¹⁰ R¹¹ ; and R¹⁰, R¹¹, R¹² and R.sup. 13 are independently H or C₁ -C₃ alkyl; provided that in compounds of Formula III, when R¹ is C₁ -C₄ alkyl and R³ is CH₃ or CF₃ then R² is benzyl or taken together with Z.
 9. A compound of claim 8 whereinR¹ is C₁ -C₃ alkyl optionally substituted with 1 to 3 F atoms or Cl atoms, O(C₁ -C₂ alkyl), S(C₁ -C₂ alkyl) or CN; C₃ -C₄ alkenyl optionally substituted with 1 to 3 F atoms or Cl atoms; C₃ -C₄ alkynyl; or C₂ -C₃ alkanoyl; R² is H, allyl, propargyl, CH(CH₃)C.tbd.CH, CHR⁷ CO₂ R⁸ or may be taken together with Z; R³ is C₁ -C₂ alkyl, C₁ -C₂ haloalkyl or N(CH₃)₂ ; and X is Cl.
 10. A compound of claim 9 whereinR¹ is CH₃ optionally substituted with 1 to 3 F atoms or Cl atoms; CH₂ CN; allyl; or propargyl; and R³ is CF₃.
 11. A compound of claim 8 wherein the compound is3-[4-chloro-2-fluoro-5-[(2-propynyl)oxy]phenyl]-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4(1H,3H)-dione; or 3-(7-chloro-5-fluoro-2,3-dihydro-2-methyl-4-benzofuranyl)-6-(dimethylamino)-1-methyl-1,3,5-triazine-2,4 (1H,3H)-dione.
 12. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 8, 9 or 10, and at least one of the following: surfactant, solid or liquid diluent.
 13. A composition suitable for controlling the growth of undesired vegetation which comprises an effective amount of a compound of claim 11, and at least one of the following: surfactant, solid or liquid diluent.
 14. A method for controlling the growth of undesired vegetation which comprises applying to the locus of the crop to be protected an effective amount of a compound of claim 8, 9, or
 10. 15. A method for controlling the growth of undesired vegetation which comprises applying to the locus of the crop to be protected an effective amount of a compound of claim
 11. 16. A method for controlling the growth of undesired vegetation which comprises applying to the locus of the crop to be protected an effective amount of a composition of claim
 12. 17. A method for controlling the growth of undesired vegetation which comprises applying to the locus of the crop to be protected an effective amount of a composition of claim
 13. 